cas 17849-38-6, 2-Chlorobenzyl alcohol | Articles data

Articles about 17849-38-6Total 207 be found

Article title
Article abstract
Author
Journal number and time
Download

Photoinduced degradation of the herbicide clomazone model reactions for natural and technical systems
The photodegradation of the herbicide clomazone in the presence of S 2O82- or of humic substances of different origin was investigated. A value of (9.4 ± 0.4) × 108 m-1 s-1 was measured for
David Gara, Pedro M.,Bosio, Gabriela N.,Arce, Valeria B.,Poulsen, Lars,Ogilby, Peter R.,Giudici, Reinaldo,Gonzalez, Monica C.,Martire, Daniel O.
p. 686 - 692
(2009)
Read Online

Selective reduction of aldehydes to alcohols by FeS-NH4Cl-CH3OH-H2O system
-
Desai,Swami,Nandurdikar
p. 931 - 933
(2002)
Read Online

Synthesis and reactivity of a hydrido CNC pincer cobalt(III) complex and its application in hydrosilylation of aldehydes and ketones
Reaction of the N-benzylidene-1-naphthylamine with CoMe(PMe3)4 afforded the hydrido CNC pincer cobalt complex CoH(PMe3)2[(C6H4)CH=N(C10H6)] (1) via double C-H bond activation. In the 1H NMR spectrum, a triplet at -18.98 ppm is the typical signal of the hydrido ligand (Co-H). Complex 1 reacted with haloalkane (CH3I and EtBr) to deliver CoX(PMe3)2((C6H4)CH=N(C10H6)) (X = I (2); Br (3)). However, the reactions of complex 1 with HCl and trifluoroacetic acid (TFA) delivered HCoCl(PMe3)2((C6H4)CH=N(C10H7)) (4) and HCo(OCOCF3)(PMe3)2((C6H4)CH=N(C10H7)) (5) with the cleavage of the Co-C(naphthyl) bond. In the 1H NMR spectra, the signals of the hydrido ligands were found at -21.31 (4) and -18.71 (5) ppm. A reaction of complex 1 with DCl was carried out to prove that the hydrogen atom eliminated to the naphthyl carbon comes from HCl. Complex 1 reacted with acetylacetone, resulting in the formation of Co(acac)(PMe3)2((C6H5)CHNH(C10H6)) (7). Complex 1 was found to be an efficient catalyst for hydrosilylation of aldehydes and ketones. The molecular structures of complex 1, 2, 4, and 7 were determined by X-ray single-crystal diffraction.
Zhou, Hongwei,Sun, Hongjian,Zhang, Shumiao,Li, Xiaoyan
p. 1479 - 1486
(2015)
Read Online

-
-
Leonard
p. 570
(1916)
Read Online

KINETICS AND MECHANISM OF OXIDATION OF SOME ARYL ALCOHOLS BY ACID BROMATE
The kinetics of oxidation of some substituted benzyl alcohols as well as the unsubstituted one by bromate ion in hydrochloric acid medium has been suggested.The results indicate that the reaction takes place by way of intermediate ester formation.Methoxy compounds react at much faster rates than the corresponding nitro substituted derivatives.The thermodynamic values associated with the equilibrium step and also for the slow step have been evaluated.A mechanism consistent with the experimental observations has been suggested.
Gupta, Kalyan Kali Sen,Kumar, Saroj Chandra,Sen, Pratik Kumar,Banerjee, Amalendu
p. 2225 - 2232
(1988)
Read Online

Efficient hydrogenation of benzaldehydes over mesopolymer-entrapped pt nanoparticles in water
Pt nanoparticles entrapped in the matrices of FDU-14 periodic mesoporous organic polymer (abbreviated as mesopolymer), prepared by a simple nd facile method, serve as an efficient catalyst for the liquid-phase hydrogenation of benzaldehydes under mild conditions. Water was confirmed to be a better choice of solvent for the hydrogenation of benzaldehydes on the Pt/FDU-14 catalyst. The highest activity (turnover frequency) was about 5700 mol-1mol -1h-1 for 3-fluorobenzaldehyde hydrogenation in water and no distinct loss of activity or selectivity was observed after the catalyst was recycled nine times. For the para-substituted benzaldehydes, the catalytic performance of Pt/FDU-14 was superior to the commercial Pt/alumina catalyst owing to the more hydrophobic nature of the FDU-based catalyst.
Li, Xiaohong,Shen, Yali,Song, Liying,Wang, Hongna,Wu, Haihong,Liu, Yueming,Wu, Peng
p. 699 - 706
(2009)
Read Online

Pt nanoparticles supported on highly dispersed TiO2 coated on SBA-15 as an efficient and recyclable catalyst for liquid-phase hydrogenation
A series of TiO2@SBA-15 composites with different TiO 2 loadings have been synthesized through hydrolysis of tetrabutyl orthotitanate via a facile sol-gel method in the presence of SBA-15 mesoporous silica. The TiO2@SBA-15 composites retain the mesostructure of the SBA-15 host, and TiO2 is highly dispersed and uniformly coated. The TiO2@SBA-15 composites serve as remarkable supports for Pt nanoparticles, which can be applied efficiently to the liquid-phase hydrogenation of benzaldehyde, its derivatives, and other unsaturated compounds under mild conditions. Of particular note is that the Pt/TiO2@SBA-15 catalysts can be reused several times without distinct loss in activity or selectivity. The more electron-deficient surface state, together with the structural and physicochemical features of Pt/TiO2@SBA-15 catalysts, would improve the catalytic activity and reusability toward the liquid-phase hydrogenation of unsaturated compounds.
Li, Xiaohong,Zheng, Wenli,Pan, Huiyan,Yu, Yin,Chen, Li,Wu, Peng
p. 9 - 19
(2013)
Read Online

Ru nanoparticles entrapped in ordered mesoporous carbons: An efficient and reusable catalyst for liquid-phase hydrogenation
Ru nanoparticles entrapped in ordered mesoporous carbons (CMK-3) served as an efficient and reusable catalyst for liquid-phase hydrogenation of benzaldehyde and its derivatives under our tested conditions (medium hydrogen pressure, room temperature, water as solvent). The Ru nanoparticles can be well stabilized by CMK-3 ordered mesoporous carbons so that the Ru leaching was below the detection limit of ICP-AES. Therefore, the Ru/CMK-3 catalyst can be used for at least five times without distinct loss in activity or selectivity for the hydrogenation of benzaldehyde. It is worthy of note that the Ru/CMK-3 catalyst was more efficient than the commercial Ru/C and homemade Ru/AC catalyst for the liquid-phase hydrogenation of benzaldehyde. The Ru/ CMK-3 catalyst can also catalyze the liquid-phase hydrogenation of nitrobenzene and its derivatives with high conversions and excellent selectivities under optimal conditions. Springer Science+Business Media New York 2013.
Ding, Yue,Li, Xiaohong,Pan, Huiyan,Wu, Peng
p. 268 - 277
(2014)
Read Online

Synthesis and biological evaluation of nigranoic acid esters as novel human neutrophil elastase inhibitors
Human neutrophil elastase (HNE) has been implicated as a major contributor in the pathogenesis of diseases, such as lung disorders and other inflammatory diseases. A series of 12 new nigranoic acid esters were regioselectively synthesised in good yields and evaluated for HNE inhibitory activity. Nigranoic acid exhibited significant inhibitory activity against HNE with the IC50 value of 3.77 M, and six esters displayed considerable inhibitory effects on HNE with IC50 values in the range of 2.61-8.95 M. The nigranoic acid esters having phenyls substituted with bromine and trimethoxyls (3h and 3b) showed stronger inhibitory activity on HNE than nigranoic acid.
Huang, Guoli,Feng, Li,Liu, Bo,He, Yi,Li, Yiming,Chen, Yegao
p. 1650 - 1656
(2015)
Read Online

Synthesis of Azido-Dienediols by Enzymatic Dioxygenation of Benzylazides: An Experimental and Theoretical Study
Allylic azides are versatile structural motifs in organic synthesis because the proximal double bond enables a [3,3]-sigmatropic rearrangement, named as the Winstein rearrangement. In this work, an experimental and theoretical study on the double Winstein rearrangement occurring in azidodienediols derived from the biocatalytic dihydroxylation of substituted benzylazides is presented. Substrates bearing a methyl group at the ortho or meta position produced exclusively rearranged exo-diendiols with the azide group anti to the diol moiety as the major constituent. In the case of para methyl substrates, an equilibrium mixture of rearranged and non-rearranged products was observed, indicating that a full conversion to the exo-dienediols is not possible within this substitution pattern. On the other hand, the presence of a chloro substituent in the diene moiety completely precluded the Winstein rearrangement to take place, giving rise exclusively to the traditional cis-cyclohexadienediols. The observed results were analyzed to determine the mechanistic and kinetic aspects and scope limitations of the reaction as a synthetic tool.
Carrera, Ignacio,Gonzalez, David,Martínez, Sebastián,Seoane, Gustavo,Umpiérrez, Diego,Veiga, Nicolás,Vila, María Agustina,de la Sovera, Victoria
supporting information

(2022/03/01)

An efficient method for the cleavage of tert-butyldiphenylsilyl ethers catalyzed by 1,3-dibromo-5,5-dimethylhydantoin
An efficient method for the deprotection of tert-butyldiphenylsilyl (TBDPS) ethers using 1,3-dibromo-5,5-dimethylhydantoin (DBH) as catalyst and dimethyl sulfoxide (DMSO) as solvent has been established. This method is useful for many kinds of compounds,
Han, Zong
p. 51 - 62
(2022/02/14)

A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides
Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H2 as terminal reducing agent are facilitated. The approach taken here enables the simultaneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered "soft"copper(I) hydrides to previously unreactive "hard"ester electrophiles and paves the way for a replacement of stoichiometric reducing agents by a catalyst and H2.
Kaicharla, Trinadh,Ngoc, Trung Tran,Teichert, Johannes F.,Tzaras, Dimitrios-Ioannis,Zimmermann, Birte M.
supporting information
p. 16865 - 16873
(2021/10/20)

Redox-active ligand based Mn(i)-catalyst for hydrosilylative ester reduction
Herein a Mn(i) catalyst bearing a redox-active phenalenyl (PLY) based ligand is reported for the efficient hydrosilylation of esters to alcohols using the inexpensive silane source polymethylhydrosiloxane (PMHS) under mild conditions. Mechanistic investigations suggest a strong ligand-metal cooperation where a ligand-based single electron transfer (SET) process initiates the reaction through Si-H bond activation.
Chakraborty, Soumi,Das, Arpan,Mandal, Swadhin K.
supporting information
p. 12671 - 12674
(2021/12/04)

Iron-catalyzed chemoselective hydride transfer reactions
A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.
Coufourier, Sébastien,Ndiaye, Daouda,Gaillard, Quentin Gaignard,Bettoni, Léo,Joly, Nicolas,Mbaye, Mbaye Diagne,Poater, Albert,Gaillard, Sylvain,Renaud, Jean-Luc
supporting information

(2021/06/07)

Method for synthesizing primary alcohol in water phase
The invention discloses a method for synthesizing primary alcohol in a water phase. The method comprises the following steps: taking aldehyde as a raw material, selecting water as a solvent, and carrying out catalytic hydrogenation reaction on the aldehyde in the presence of a water-soluble catalyst to obtain the primary alcohol, wherein the catalyst is a metal iridium complex [Cp*Ir(2,2'-bpyO)(OH)][Na]. Water is used as the solvent, so that the use of an organic solvent is avoided, and the method is more environment-friendly; the reaction is carried out at relatively low temperature and normal pressure, and the reaction conditions are mild; alkali is not needed in the reaction, so that generation of byproducts is avoided; and the conversion rate of the raw materials is high, and the yield of the obtained product is high. The method not only has academic research value, but also has a certain industrialization prospect.
-
Paragraph 0031-0032

(2021/07/14)

Ambient-pressure highly active hydrogenation of ketones and aldehydes catalyzed by a metal-ligand bifunctional iridium catalyst under base-free conditions in water
A green, efficient, and high active catalytic system for the hydrogenation of ketones and aldehydes to produce corresponding alcohols under atmospheric-pressure H2 gas and ambient temperature conditions was developed by a water-soluble metal–ligand bifunctional catalyst [Cp*Ir(2,2′-bpyO)(OH)][Na] in water without addition of a base. The catalyst exhibited high activity for the hydrogenation of ketones and aldehydes. Furthermore, it was worth noting that many readily reducible or labile functional groups in the same molecule, such as cyan, nitro, and ester groups, remained unchanged. Interestingly, the unsaturated aldehydes can be also selectively hydrogenated to give corresponding unsaturated alcohols with remaining C=C bond in good yields. In addition, this reaction could be extended to gram levels and has a large potential of wide application in future industrial.
Wang, Rongzhou,Yue, Yuancheng,Qi, Jipeng,Liu, Shiyuan,Song, Ao,Zhuo, Shuping,Xing, Ling-Bao
p. 1 - 7
(2021/05/17)

Whole seeds of Bauhinia variegata L. (Fabaceae) as an efficient biocatalyst for benzyl alcohol preparations from benzaldehydes
Whole seeds of Bauhinia variegata L. (Fabaceae) were utilized as a biological reducer to transform benzaldehyde into benzyl alcohol. The effects of some variables such as temperature, the load of substrate and co-solvent, were established to optimize the reductive process. Utilizing the optimal reaction conditions, a laboratory-scale reaction (final concentration of the substrate: 21.2 mM) was performed to obtain benzyl alcohol (conversion: 95%; isolated yield: 49%; productivity: 1.11 g L?1 or 0.046 g L?1h?1 of benzyl alcohol). In addition, using these optimal conditions, fourteen substituted benzaldehydes were reduced, with a conversion achieved to their corresponding benzyl alcohols ranging from 62% to >99% (isolated yields from 7% to 70%). Moreover, useful building blocks by the synthesis of the drugs and important commercial products were also obtained. The scope, limitations and advantages of this new biocatalytic synthetic method are also discussed.
Aimar, Mario L.,Bordón, Daniela L.,Díaz Panero, Mariángeles,Decarlini, María F.,Demmel, Gabriel I.,Rossi, Laura I.,Vázquez, Ana M.
(2021/08/03)

Homoleptic cobalt(II) phenoxyimine complexes for hydrosilylation of aldehydes and ketones without base activation of cobalt(II)
Air-stable, easy to prepare, homoleptic cobalt(II) complexes bearing pendant-modified phenoxyimine ligands were synthesized and determined. The complexes exhibited high catalytic performance for reducing aldehydes and ketones via catalytic hydrosilylation, where a hydrosilane and a catalytic amount of the cobalt(II) complex were added under base-free conditions. The reaction proceeded even in the presence of excess water, and excellent functional-group tolerance was observed. Subsequent hydrolysis gave the alcohol in high yields. Moreover, H2O had a critical role in activation of the Co(II) catalyst with hydrosilane. Several additional results also indicated that the cobalt(II) center acts as an active catalyst in the hydrosilylation of aldehydes and ketones.
Hori, Momoko,Ishikawa, Ryuta,Koga, Yuji,Matsubara, Kouki,Mitsuyama, Tomoaki,Shin, Sayaka
p. 1379 - 1387
(2021/05/29)

Heterogeneous Catalyzed Chemoselective Reductive Amination of Halogenated Aromatic Aldehydes
The chemoselective conversion of a specific functional group in a multifunctional substrate is of great importance in the chemical industry to obtain cost efficient, sustainable and waste free processes. This work focuses on the chemoselective amination of halogenated aromatic aldehydes with dimethyl amine towards halogenated aromatic amines, a raw material used in the production of for example agrochemical active ingredients. It was found that by combining palladium, a metal known for dehalogenation reactions, and copper, known for its direct hydrogenation of aldehydes to alcohols, in one heterogeneous bimetallic catalyst, a synergistic effect is obtained. By depositing copper onto a palladium on carbon catalyst with a Cu/Pd ratio of at least 1 : 1, the yield could be increased from 66 % (Pd/C) to 98 % (PdCu/C). Moreover, this highly active and stable catalyst also showed suppressed dehalogenation side-reactions in several other chemical conversions such as hydrogenation of nitro functional groups and hydrogenation of aldehydes.
Dumoleijn, Kim N. R.,Villa, Alberto,Marelli, Marcello,Prati, Laura,Moonen, Kristof,Stevens, Christian V.
p. 3021 - 3026
(2021/05/18)

Synthesis and catalytic activity of N-heterocyclic silylene (NHSi) iron (II) hydride for hydrosilylation of aldehydes and ketones
A novel silylene supported iron hydride [Si, C]FeH (PMe3)3 (1) was synthesized by C (sp3)-H bond activation with zero-valent iron complex Fe (PMe3)4. Complex 1 was fully characterized by spectroscopic methods and single crystal X-ray diffraction analysis. To the best of our knowledge, 1 is the first example of silylene-based hydrido chelate iron complex produced through activation of the C (sp3)?H bond. It was found that complex 1 exhibited excellent catalytic activity for hydrosilylation of aldehydes and ketones. The catalytic system showed good tolerance and catalytic activity for the substrates with different functional groups on the benzene ring. It is worth mentioning that, the experimental results showed that both ketones and aldehydes could be reduced in good to excellent yields under the same catalytic conditions. Based on the experiments and literature reports, a possible catalytic mechanism was proposed.
Du, Xinyu,Qi, Xinghao,Li, Kai,Li, Xiaoyan,Sun, Hongjian,Fuhr, Olaf,Fenske, Dieter
(2021/05/29)

Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride
A one-pot reductive amination of aldehydes and ketones with NaBH4 was developed with a view to providing efficient, economical and greener synthetic conditions. A recyclable iron-based Lewis catalyst, Aquivion-Fe, was used to promote imine formation in cyclopentyl methyl ether, followed by the addition of a small amount of methanol to the reaction mixture to enable C=N reduction by NaBH4. The protocol, applied to a wide number of amines and carbonyl compounds, resulted in ever complete conversion of these latter with excellent chemoselectivity towards the expected amination products in the most cases. Isolated yields, determined for a selection of the screened substrates, were found consistent with the previously obtained conversion and selectivity data. Cinacalcet, an important active pharmaceutical ingredient, was efficiently prepared by the title procedure.
Airoldi, Veronica,Piccolo, Oreste,Roda, Gabriella,Appiani, Rebecca,Bavo, Francesco,Tassini, Riccardo,Paganelli, Stefano,Arnoldi, Sebastiano,Pallavicini, Marco,Bolchi, Cristiano
supporting information
p. 162 - 168
(2019/12/11)

Continuous-Flow Amide and Ester Reductions Using Neat Borane Dimethylsulfide Complex
Reductions of amides and esters are of critical importance in synthetic chemistry, and there are numerous protocols for executing these transformations employing traditional batch conditions. Notably, strategies based on flow chemistry, especially for amide reductions, are much less explored. Herein, a simple process was developed in which neat borane dimethylsulfide complex (BH3?DMS) was used to reduce various esters and amides under continuous-flow conditions. Taking advantage of the solvent-free nature of the commercially available borane reagent, high substrate concentrations were realized, allowing outstanding productivity and a significant reduction in E-factors. In addition, with carefully optimized short residence times, the corresponding alcohols and amines were obtained in high selectivity and high yields. The synthetic utility of the inexpensive and easily implemented flow protocol was further corroborated by multigram-scale syntheses of pharmaceutically relevant products. Owing to its beneficial features, including low solvent and reducing agent consumption, high selectivity, simplicity, and inherent scalability, the present process demonstrates fewer environmental concerns than most typical batch reductions using metal hydrides as reducing agents.
?tv?s, Sándor B.,Kappe, C. Oliver
p. 1800 - 1807
(2020/02/27)

Synthesis and structure activity relationships of cyanopyridone based anti-tuberculosis agents
Mycobacterium tuberculosis, the causative agent of tuberculosis, relies on thymidylate kinase (MtbTMPK) for the synthesis of thymidine triphosphates and thus also DNA synthesis. Therefore, this enzyme constitutes a potential Achilles heel of the pathogen. Based on a previously reported MtbTMPK 6-aryl-substituted pyridone inhibitor and guided by two co-crystal structures of MtbTMPK with pyridone- and thymine-based inhibitors, we report the synthesis of a series of aryl-shifted cyanopyridone analogues. These compounds generally lacked significant MtbTMPK inhibitory potency, but some analogues did exhibit promising antitubercular activity. Analogue 11i demonstrated a 10-fold increased antitubercular activity (MIC H37Rv, 1.2 μM) compared to literature compound 5. Many analogues with whole-cell antimycobacterial activity were devoid of significant cytotoxicity.
Boshoff, Helena I. M.,Caljon, Guy,Forbes, He Eun,Hulpia, Fabian,Jian, Yanlin,Munier-Lehmann, Héle?ne,Risseeuw, Martijn D. P.,Van Calenbergh, Serge
(2020/07/06)

Cyclopentadienone iron tricarbonyl complexes-catalyzed hydrogen transfer in water
The development of efficient and low-cost catalytic systems is important for the replacement of robust noble metal complexes. The synthesis and application of a stable, phosphine-free, water-soluble cyclopentadienone iron tricarbonyl complex in the reduction of polarized double bonds in pure water is reported. In the presence of cationic bifunctional iron complexes, a variety of alcohols and amines were prepared in good yields under mild reaction conditions.
Coufourier, Sébastien,Gaillard, Sylvain,Mbaye, Mbaye Diagne,Ndiaye, Daouda,Renaud, Jean-Luc
supporting information

(2020/01/28)

Chemoselective transfer hydrogenation of aromatic and heterocyclic aldehydes by green chemically prepared cobalt oxide nanoparticles
A new surfactant (quercetin) assisted hydrothermal method is used for the preparation of phase pure cobalt oxide (Co3O4) nanoparticles (Nps). The quercetin acted well as surfactant in producing size controlled Nps. The produced Nps were extensively characterized by various techniques to reveal its chemical composition, structure, morphology, size and thermal behavior. The main objective of the study is to employ the prepared material as heterogeneous catalyst for hydrogenation of therapeutically important aldehydes. The capability of the catalyst is appear to be good, since the yield of alcohols from structurally different aldehydes is adequate with short period of time. Also the catalyst is recyclable, stable, no need of addition of ligands for activation and environmentally benign.
Krishnaveni,Lakshmi,Kaveri,Kadirvelu
(2020/09/16)

Pyridine: N-oxide promoted hydrosilylation of carbonyl compounds catalyzed by [PSiP]-pincer iron hydrides
Five [PSiP]-pincer iron hydrides 1-5, [(2-Ph2PC6H4)2HSiFe(H)(PMe3)2 (1), (2-Ph2PC6H4)2MeSiFe(H)(PMe3)2 (2), (2-Ph2PC6H4)2PhSiFe(H)(PMe3)2 (3), (2-(iPr)2PC6H4)2HSiFe(H)(PMe3) (4), and (2-(iPr)2PC6H4)2MeSiFe(H)(PMe3)2 (5)], were used as catalysts to study the effects of pyridine N-oxide and the electronic properties of [PSiP]-ligands on the catalytic hydrosilylation of carbonyl compounds. It was proved for the first time that this catalytic process could be promoted with pyridine N-oxide as the initiator at 30 °C because the addition of pyridine N-oxide is beneficial for the formation of an unsaturated hydrido iron complex, which is the key intermediate in the catalytic mechanism. Complex 4 as the best catalyst shows excellent catalytic performance. Among the five complexes, complex 3 was new and the molecular structure of complex 3 was determined by single crystal X-ray diffraction. A proposed mechanism was discussed.
Chang, Guoliang,Fenske, Dieter,Fuhr, Olaf,Li, Xiaoyan,Sun, Hongjian,Xie, Shangqing,Yang, Wenjing,Zhang, Peng
p. 9349 - 9354
(2020/09/09)

Bimetallic Bis-NHC-Ir(III) Complex Bearing 2-Arylbenzo[d]oxazolyl Ligand: Synthesis, Catalysis, and Bimetallic Effects
Herein, an unprecedented bimetallic bis-NHC Cp*Ir complex 1 bearing 2-arylbenzo[d]oxazolyl and NHC ligands is reported. A significant increase in activity was observed for N-methylation of amines and reduction of aldehydes with MeOH catalyzed by 1 compared to the monometallic analogues (2-11). Under the optimal conditions, it showed to be highly effective in N-methylation of nitroarenes with MeOH as both C1 and H2 source. Substrates, including aromatic amines, ketones, and nitro compounds with various functional groups, can be well-tolerated. Mechanistic studies and DFT calculation highlight the significance of bimetallic centers cooperativity.
Huang, Shuang,Hong, Xi,Cui, He-Zhen,Zhan, Bing,Li, Zhi-Ming,Hou, Xiu-Feng
p. 3514 - 3523
(2020/10/09)

Linear β-amino alcohol catalyst anchored on functionalized magnetite nanoparticles for enantioselective addition of dialkylzinc to aromatic aldehydes
A linear β-amino alcohol ligand, previously found to be a very efficient catalyst for enantioselective addition of dialkylzinc to aromatic aldehydes, has been anchored on differently functionalized superparamagnetic core-shell magnetite-silica nanoparticles (1a and 1b). Its catalytic activity in the addition of dialkylzinc to aldehydes has been evaluated, leading to promising results, especially in the case of 1b for which the recovery by simple magnetic decantation and reuse was successfully verified. This journal is
Ciprioti, Stefano Vecchio,De Angelis, Martina,Di Pietro, Federica,Iannoni, Marika,Pilloni, Luciano,Primitivo, Ludovica,Ricelli, Alessandra,Righi, Francesco,Righi, Giuliana,Sappino, Carla,Suber, Lorenza
p. 29688 - 29695
(2020/10/26)

A General Method for Photocatalytic Decarboxylative Hydroxylation of Carboxylic Acids
A general and practical method for decarboxylative hydroxylation of carboxylic acids was developed through visible light-induced photocatalysis using molecular oxygen as the green oxidant. The addition of NaBH4 to in situ reduce the unstable peroxyl radical intermediate much broadened the substrate scope. Different sp3 carbon-bearing carboxylic acids were successfully employed as substrates, including phenylacetic acid-type substrates, as well as aliphatic carboxylic acids. This transformation worked smoothly on primary, secondary, and tertiary carboxylic acids.
Khan, Shah Nawaz,Zaman, Muhammad Kashif,Li, Ruining,Sun, Zhankui
p. 5019 - 5026
(2020/05/01)

1-D manganese(ii)-terpyridine coordination polymers as precatalysts for hydrofunctionalisation of carbonyl compounds
Reductive catalysis with earth-abundant metals is currently of increasing importance and shows potential in replacing precious metal catalysis. In this work, we revealed catalytic hydroboration and hydrosilylation of ketones and aldehydes achieved by a structurally defined manganese(ii) coordination polymer (CP) as a precatalyst under mild conditions. The manganese-catalysed methodology can be applied to a range of functionalized aldehydes and ketones with turnover numbers (TON) of up to 990. Preliminary results on the regioselective catalytic hydrofunctionalization of styrenes by the Mn-CP catalyst are also presented.
Johnson, Jahvon,Li, Sihan,Mo, Zixuan,Neary, Michelle C.,Zeng, Haisu,Zhang, Guoqi,Zheng, Shengping
supporting information
p. 2610 - 2615
(2020/03/05)

Palladium-Catalyzed Selective Reduction of Carbonyl Compounds
Two new examples of structurally characterized β-diketiminate analogues i.e., conjugated bis-guanidinate (CBG) supported palladium(II) complexes, [LPdX]2; [L= {(ArHN)(ArN)–C=N–C=(NAr)(NHAr)}; Ar = 2,6-Et2-C6H3], X = Cl (1), Br (2) have been reported. The synthesis of complexes 1–2 was achieved by two methods. Method A involves deprotonation of LH by nBuLi followed by the treatment of LLi (insitu formed) with PdCl2 in THF, which afforded compound 1 in good yield (75 %). In Method B, the reaction between free LH and PdX2 (X = Cl or Br) in THF allowed the formation of complexes 1 (Yield 73 %) and 2 (Yield 52 %), respectively. Moreover, these complexes were characterized thoroughly by several spectroscopic techniques (1H, 13C NMR, UV/Vis, FT-IR, and HRMS), including single-crystal X-ray structural and elemental analyses. In addition, we tested the catalytic activity of these complexes 1–2 for the hydroboration of carbonyl compounds with pinacolborane (HBpin). We observed that compound 1 exhibits superior catalytic activity when compared to 2. Compound 1 efficiently catalyzes various aldehydes and ketones under solvent-free conditions. Furthermore, both inter- and intramolecular chemoselectivity hydroboration of aldehydes over other functionalities have been established.
Sarkar, Nabin,Mahato, Mamata,Nembenna, Sharanappa
p. 2295 - 2301
(2020/05/18)

Erratum: Redox-Noninnocent Ligand-Supported Vanadium Catalysts for the Chemoselective Reduction of C=X (X = O, N) Functionalities (Journal of the American Chemical Society (2019) 141:38 (15230-15239) DOI: 10.1021/jacs.9b07062)
Pages 15232, 15233, and 15236. In the original paper, the doublet wave functions for 21 and 21a/21b were incorrectly (Figure Presented). reported as spin-contaminated in sections 2.3 and 2.8 (Figure 3 and Scheme 9, respectively.) This comes from the incorrectly reported expected eigenvalue of 0.75 for the spin-squared operator ??2? for the antiferromagnetically coupled doublet |↓?L|↑↑?V state (originally given in the Supporting Information). The correct expected eigenvalue for the |↓?L|↑↑?V state should be 1.75. The wave functions for 21 and 21a/21b (eigenvalues 1.79 and 1.77/1.66, respectively) are therefore not spincontaminated. The corrected Figure 3 and Scheme 9 are presented below. A corrected Supporting Information file is also provided. The corrections do not affect any of the conclusions of the Article, but slightly decrease the gap between the quartet and doublet spin surfaces. Scheme 3 has been also corrected to reflect the fact that (CH3)3SiCH2 ? radicals can only react based on spin conservation.
Zhang, Guoqi,Wu, Jing,Zheng, Shengping,Neary, Michelle C.,Mao, Jincheng,Flores, Marco,Trovitch, Ryan J.,Dub, Pavel A.
supporting information
p. 16507 - 16509
(2020/10/14)

Storing redox equivalent in the phenalenyl backbone towards catalytic multi-electron reduction
Storing and transferring electrons for multi-electron reduction processes are considered to be the key steps in various important chemical and biological transformations. In this work, we accomplished multi-electron reduction of a carboxylic acid via a hydrosilylation pathway where a redox-active phenalenyl backbone in Co(PLY-O,O)2(THF)2, stores electrons and plays a preponderant role in the entire process. This reduction proceeds by single electron transfer (SET) from the mono-reduced ligand backbone leading to the cleavage of the Si-H bond. Several important intermediates along the catalytic reduction reaction have been isolated and well characterized to prove that the redox equivalent is stored in the form of a C-H bond in the PLY backbone via a ligand dearomatization process. The ligand's extensive participation in storing a hydride equivalent has been conclusively elucidated via a deuterium labelling experiment. This is a rare example where the ligand orchestrates the multielectron reduction process leaving only the metal to maintain the conformational requirements and fine tunes the electronics of the catalyst.
Bhunia, Mrinal,Sahoo, Sumeet Ranjan,Shaw, Bikash Kumar,Vaidya, Shefali,Pariyar, Anand,Vijaykumar, Gonela,Adhikari, Debashis,Mandal, Swadhin K.
p. 7433 - 7441
(2019/08/15)

Enzymatic One-Step Reduction of Carboxylates to Aldehydes with Cell-Free Regeneration of ATP and NADPH
The direct generation of aldehydes from carboxylic acids is often a challenging synthetic task but undoubtedly attractive in view of abundant supply of such feedstocks from nature. Though long known, biocatalytic carboxylate reductions are at an early stage of development, presumably because of their co-factor requirement. To establish an alternative to whole-cell-based carboxylate reductions which are limited by side reactions, we developed an in vitro multi-enzyme system that allows for quantitative reductions of various carboxylic acids with full recycling of all cofactors and prevention of undesired over-reductions. Regeneration of adenosine 5′-triphosphate is achieved through the simultaneous action of polyphosphate kinases from Meiothermus ruber and Sinorhizobium meliloti and β-nicotinamide adenine dinucleotide 2′-phosphate is reduced by a glucose dehydrogenase. Under these conditions and in the presence of the carboxylate reductases from Neurospora crassa or Nocardia iowensis, various aromatic, heterocyclic and aliphatic carboxylic acids were quantitatively reduced to the respective aldehydes.
Strohmeier, Gernot A.,Eitelj?rg, Inge C.,Schwarz, Anna,Winkler, Margit
p. 6119 - 6123
(2019/04/13)

Diaminodiphosphine tetradentate ligand and ruthenium complex thereof, and preparation methods and applications of ligand and complex
The invention discloses a diaminodiphosphine tetradentate ligand and a ruthenium complex thereof, and preparation methods and applications of the ligand and the complex, and provides a ruthenium complex represented by a formula I, wherein L is a diaminodiphosphine tetradentate ligand represented by a formula II, and X and Y are respectively and independently chlorine ion, bromine ion, iodine ion,hydrogen negative ion or BH4. According to the present invention, the ruthenium complex exhibits excellent catalytic activity in the catalytic hydrogenation reactions of ester compounds, has high yield and high chemical selectivity, is compatible with conjugated and non-conjugated carbon-carbon double bond, carbon-carbon triple bond, epoxy, halogen, carbonyl and other functional groups, and hasgreat application prospects.
-
Paragraph 0301-0304

(2019/11/04)

Nanoporous Na+-montmorillonite perchloric acid as an efficient and recyclable catalyst for the chemoselective protection of hydroxyl groups
Nanoporous Na+-montmorillonite perchloric acid as a novel heterogeneous reusable solid acid catalyst was easily prepared by treatment of Na+-montmorillonite as a cheap and commercially available support with perchloric acid. The catalyst was characterized using a variety of techniques including X-ray powder diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), thermogravimetric analysis (TGA), energy dispersive X-ray spectroscopy (EDX), pH analysis and determination of the Hammett acidity function. The prepared reagent showed excellent catalytic activity for the chemoselective conversion of alcohols and phenols to their corresponding trimethylsilyl ethers with 1,1,1,3,3,3-hexamethyldisilazane (HMDS) at room temperature. Deprotection of the resulting trimethylsilyl ethers can also be carried out using the same catalyst in ethanol. All reactions were performed under mild and completely heterogeneous reaction conditions in good to excellent yields. The notable advantages of this protocol are: short reaction times, high yields, availability and low cost of the reagent, easy work-up procedure and the reusability of the catalyst during a simple filtration.
Mashhadinezhad, Maryam,Shirini, Farhad,Mamaghani, Manouchehr
p. 2099 - 2107
(2019/01/03)

DMSO-Triggered Complete Oxygen Transfer Leading to Accelerated Aqueous Hydrolysis of Organohalides under Mild Conditions
Addition of DMSO is found to greatly accelerate the aqueous hydrolysis of organohalides to alcohols, providing a neutral, more efficient, milder and more economic process. Mechanistic studies using 18O-DMSO and 18O-H2O showed that, contrary to the opinion that DMSO works as a dipolar solvent to enhance water's nucleophilicity, the accelerating effect comes from a complete oxygen transfer from DMSO to organohalides through generation of ROS+Me2?X? salts through C?O bond formation, followed by O?S bond disassociative hydrolysis of ROS+Me2?X? with water. This method is applicable to a wide range of organohalides and thus may have potential for practical industrial application, owing to easy recovery of DMSO from the H2O/DMSO mixture by regular vacuum rectification.
Liu, Haicheng,Liu, Jianping,Cheng, Xiaokai,Jia, Xiaojuan,Yu, Lei,Xu, Qing
p. 2994 - 2998
(2019/01/04)

Biphenyl tridentate ligand ruthenium complex and production method and application thereof
The invention relates to production methods of a novel biphenyl tridentate ligand and a ruthenium complex of the novel biphenyl tridentate ligand and application of the ruthenium complex of the novelbiphenyl tridentate ligand in reaction of hydrogenation of an ester compound to an alcohol compound. A method for using the biphenyl tridentate ligand ruthenium complex for catalyzing hydrogenation ofthe ester compound to the alcohol compound is characterized by comprising the steps of using the biphenyl tridentate ligand ruthenium complex which is 0.001-0.1 mol% of the amount of substance of theester compound as a catalyst, adding alkali which is 1-10 mol% of the amount of substance of the ester compound, and catalyzing hydrogenation of the ester compound to the corresponding alcohol compound under conditions of 60-100 DEG C and 30-70 MPa hydrogen pressure. The biphenyl tridentate ligand and the ruthenium complex of the biphenyl tridentate ligand are convenient to produce and stable instructure, and the ruthenium complex of the biphenyl tridentate ligand shows excellent catalytic activity in the hydrogenation reaction of the ester compound. The defects of rigorous reaction conditions of high temperature, high pressure and the like needed by existing homogeneous or heterogeneous catalytic system hydrogenated fat compounds and high dosages of catalysts are overcome, the dosage ofthe catalyst is little, the reaction conditions are mild, the selectivity of the reaction is good, and the economical efficiency and the safety of the production system are improved.
-
Paragraph 0108-0114

(2019/07/17)

Polypyridyl iridium(III) based catalysts for highly chemoselective hydrogenation of aldehydes
Iridium-catalyzed transfer hydrogenation (TH) of carbonyl compounds using HCOOR (R = H, Na, NH4) as a hydrogen source is a pivotal process as it provides the clean process and is easy to execute. However, the existing highly efficient iridium catalysts work at a narrow pH; thus, does not apply to a wide variety of substrates. Therefore, the development of a new catalyst which works at a broad pH range is essential as it can gain a broader scope of utilization. Here we report highly efficient polypyridyl iridium(III) catalysts, [Ir(tpy)(L)Cl](PF6)2 {where tpy = 2,2′:6′,2′'-Terpyridine, L = phen (1,10-Phenanthroline), Me2phen (4,7-Dimethyl-1,10-phenanthroline), Me4phen (3,4,7,8-Tetramethyl-1,10-phenanthroline), Me2bpy (4,4′-Dimethyl-2–2′-dipyridyl)} for the chemoselective reduction of aldehydes to alcohols in aqueous ethanol and sodium formate as the hydride source. The reaction can be carried out efficiently in broad pH ranges, from pH 6 to 11. These catalysts are air stable, easy to prepare using commercially available starting materials, and are highly applicable for a wide range of substrates, such as electron-rich or deficient (hetero)arenes, halogens, phenols, alkoxy, ketones, esters, carboxylic acids, cyano, and nitro groups. Particularly, acid and hydroxy groups containing aldehydes were reduced successfully in basic and acidic reaction conditions, demonstrating the efficiency of the catalyst in a broad pH range with high conversion rates under microwave irradiation.
Pandrala, Mallesh,Resendez, Angel,Malhotra, Sanjay V.
p. 283 - 288
(2019/09/30)

A method of synthesis of primary alcohol (by machine translation)
The invention discloses a method for synthesizing a primary alcohol, using transition metal catalysis, the use of isopropanol as a hydrogen source to synthesize primary alcohol, the reaction not only using a cheap, environmental protection of isopropanol as a hydrogen source and solvent, and has high yield, environmental protection and the like, so that the reaction has broad prospects for development. (by machine translation)
-
Paragraph 0065; 0066; 0067; 0068

(2019/03/17)

Efficient transfer hydrogenation of carbonyl compounds catalyzed by selenophenolato hydrido iron(II) complexes
Selenophenolato hydrido iron(II) complexes 1–3 cis-[(H)(SeAr)Fe(PMe3)4] (Ar = C6H5 (1), p-MeOC6H4 (2) and o-MeC6H4 (3)) could catalyze transfer hydrogenation of aldehydes and ketones. Among the three complexes, catalyst 1 exhibited the highest catalytic activity. The catalytic reactions took place under very mild conditions, using isopropanol as solvent and hydrogen source, tBuONa as base under 60–80 °C. This catalytic system has good tolerance for many functional groups, such as halides, C[dbnd]C double bonds, nitro groups and cyano groups at the phenyl ring of the substrates.
Wang, Yangyang,Du, Zhengyin,Zheng, Tingting,Sun, Hongjian,Li, Xiaoyan
p. 32 - 35
(2019/03/06)

Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C?O Bond Formation
A combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C?O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl-substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed-etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the aryl boronic acid and oxalic acid.
Estopi?á-Durán, Susana,Donnelly, Liam J.,Mclean, Euan B.,Hockin, Bryony M.,Slawin, Alexandra M. Z.,Taylor, James E.
supporting information
p. 3950 - 3956
(2019/02/16)

Ambient-pressure hydrogenation of ketones and aldehydes by a metal-ligand bifunctional catalyst [Cp*Ir(2,2′-bpyO)(H2O)] without using base
An efficient catalytic system for hydrogenation of ketones and aldehydes using a Cp*Ir complex [Cp*Ir(2,2′-bpyO)(H2O)] bearing a bipyridine-based functional ligand as catalyst has been developed. A wide variety of secondary and primary alcohols were synthesized by the catalyzed hydrogenation of ketones and aldehydes under facile atmospheric-pressure without a base. The catalyst also displays an excellent chemoselectivity towards other carbonyl functionalities and unsaturated motifs. This catalytic system exhibits high activity for hydrogenation of ketones and aldehydes with H2 gas.
Wang, Rongzhou,Qi, Jipeng,Yue, Yuancheng,Lian, Zhe,Xiao, Haibin,Zhuo, Shuping,Xing, Lingbao
(2019/07/30)

Synthesis and evaluation of novel purple acid phosphatase inhibitors
Transgenic studies in animals have demonstrated a direct association between the level of expression of purple acid phosphatase (PAP; also known as tartrate-resistant acid phosphatase) and the progression of osteoporosis. Consequently, PAP has emerged as
Hussein, Waleed M.,Feder, Daniel,Schenk, Gerhard,Guddat, Luke W.,McGeary, Ross P.
p. 61 - 71
(2019/01/30)

Synthesis and Catalytic Activity of Iron Hydride Ligated with Bidentate N-Heterocyclic Silylenes for Hydroboration of Carbonyl Compounds
We report the synthesis of a novel bidentate N-heterocyclic silylene (NHSi) ligand, N-(LSi:)-N-methyl-2-pyridinamine (1) (L = PhC(NtBu)2), and the first bischelate disilylene iron hydride, [(Si,N)(Si,C)Fe(H)(PMe3)] (2), and monosilylene iron hydride, [(Si,C)Fe(H)(PMe3)3] (2′), through Csp2-H activation of the NHSi ligand. Compounds 1 and 2 were fully characterized by spectroscopic methods and single-crystal X-ray diffraction analysis. Density functional theory calculations indicated the multiple-bond character of the Fe-Si bonds and the π back-donation from Fe(II) to the Si(II) center. Moreover, the strong donor character of ligand 1 enables 2 to act as an efficient catalyst for the hydroboration reaction of carbonyl compounds at room temperature. Chemoselective hydroboration is attained under these conditions. This might be the first example of hydroboration of ketones and aldehydes catalyzed by a silylene hydrido iron complex. A catalytic mechanism was suggested and partially experimentally verified.
Qi, Xinghao,Zheng, Tingting,Zhou, Junhao,Dong, Yanhong,Zuo, Xia,Li, Xiaoyan,Sun, Hongjian,Fuhr, Olaf,Fenske, Dieter
p. 268 - 277
(2019/01/21)

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans
An intermolecular addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermolecular alkyl radical addition to a carbonyl group followed by an intramolecular alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR analysis. The mechanism is investigated by KIE experiments and control experiments. This method could provide rapid and practical access to the key intermediate of TAM-16, a safe and potent antibacterial agent for treating tuberculosis, and, therefore, is of great importance for organic synthesis and the pharmaceutical industry.
Zheng, Hong-Xing,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao
supporting information
p. 3310 - 3313
(2018/06/11)

Selective ligand-free cobalt-catalysed reduction of esters to aldehydes or alcohols
Cobalt(ii) salts combined with NaBHEt3 and eventually a base catalyse efficiently and selectively the reduction of esters to aldehydes or alcohols through hydrosilylation by using phenylsilane. Catalyst characterisation by XRD, XPS, TEM and STEM analyses indicates the materials were partially crystalline with the presence of cobalt nanoparticles. Control experiments suggested low valent Co(0) was the active catalytic species involved.
Rysak, Vincent,Descamps-Mandine, Armel,Simon, Pardis,Blanchard, Florent,Burylo, Laurence,Trentesaux, Martine,Vandewalle, Maxence,Collière, Vincent,Agbossou-Niedercorn, Francine,Michon, Christophe
p. 3504 - 3512
(2018/07/29)

Transfer Hydrogenation of Aldehydes and Ketones with Isopropanol under Neutral Conditions Catalyzed by a Metal-Ligand Bifunctional Catalyst [Cp?Ir(2,2′-bpyO)(H2O)]
A Cp?Ir complex bearing a functional bipyridonate ligand [Cp?Ir(2,2′-bpyO)(H2O)] was found to be a highly efficient and general catalyst for transfer hydrogenation of aldehydes and chemoselective transfer hydrogenation of unsaturated aldehydes with isopropanol under neutral conditions. It was noteworthy that many readily reducible or labile functional groups such as nitro, cyano, ester, and halide did not undergo any change under the reaction conditions. Furthermore, this catalytic system exhibited high activity for transfer hydrogenation of ketones with isopropanol. Notably, this research exhibited new potential of metal-ligand bifunctional catalysts for transfer hydrogenation.
Wang, Rongzhou,Tang, Yawen,Xu, Meng,Meng, Chong,Li, Feng
p. 2274 - 2281
(2018/02/23)

Methanol as hydrogen source: Transfer hydrogenation of aromatic aldehydes with a rhodacycle
A cyclometalated rhodium complex has been shown to perform highly selective and efficient reduction of aldehydes, deriving the hydrogen from methanol. With methanol as both the solvent and hydrogen donor under mild conditions and an open atmosphere, a wide range of aromatic aldehydes were reduced to the corresponding alcohols, without affecting other functional groups.
Aboo, Ahmed H.,Bennett, Elliot L.,Deeprose, Mark,Robertson, Craig M.,Iggo, Jonathan A.,Xiao, Jianliang
supporting information
p. 11805 - 11808
(2018/11/10)

Transfer hydrogenation of aldehydes catalyzed by silyl hydrido iron complexes bearing a [PSiP] pincer ligand
The synthesis and characterization of a series of silyl hydrido iron complexes bearing a pincer-type [PSiP] ligand (2-R2PC6H4)2SiH2 (R = Ph (1) and iPr (5)) or (2-Ph2PC6H4)2SiMeH (2) were reported. Preligand 1 reacted with Fe(PMe3)4 to afford complex ((2-Ph2PC6H4)SiH)Fe(H)(PMe3)2 (3) in toluene, which was structurally characterized by X-ray diffraction. ((2-iPr2PC6H4)SiH)Fe(H)(PMe3) (6) could be obtained from the reaction of preligand 5 with Fe(PMe3)4 in toluene. Furthermore, complex ((2-iPr2PC6H4)Si(OMe))Fe(H)(PMe3) (7) was isolated by the reaction of complex 6 with 2 equiv. MeOH in THF. The molecular structure of complex 7 was also determined by single-crystal X-ray analysis. Complexes 3, 4, 6 and 7 showed good to excellent catalytic activity for transfer hydrogenation of aldehydes under mild conditions, using 2-propanol as both solvent and hydrogen donor. α,β-Unsaturated aldehydes could be selectively reduced to corresponding α,β-unsaturated alcohols. The catalytic activity of penta-coordinate complex 6 or 7 is stronger than that of hexa-coordinate complex 3 or 4.
Zhang, Peng,Li, Xiaoyan,Qi, Xinghao,Sun, Hongjian,Fuhr, Olaf,Fenske, Dieter
p. 14092 - 14099
(2018/04/25)

Cobalt(II) Coordination Polymer as a Precatalyst for Selective Hydroboration of Aldehydes, Ketones, and Imines
Highly effective hydroboration precatalyst is developed based on a cobalt(II)-terpyridine coordination polymer (CP). The hydroboration of ketones, aldehydes, and imines with pinacolborane (HBpin) has been achieved using the recyclable CP catalyst in the presence of an air-stable activator. A wide range of substrates containing polar C=O or C=N bonds have been hydroborated selectively in excellent yields under ambient conditions.
Wu, Jing,Zeng, Haisu,Cheng, Jessica,Zheng, Shengping,Golen, James A.,Manke, David R.,Zhang, Guoqi
p. 9442 - 9448
(2018/07/05)

Synthesis of silyl iron hydride: Via Si-H activation and its dual catalytic application in the hydrosilylation of carbonyl compounds and dehydration of benzamides
The hydrido silyl iron complex (o-Ph2PC6H4SiMe2)Fe(PMe3)3H (2) was obtained via the activation of the Si-H bond of the bidentate silyl ligand o-Ph2P(C6H4)SiMe2H (1) by Fe(PMe3)4. 2 showed good to excellent catalytic activity in both the reduction of aldehydes/ketones and the dehydration of benzamide. In addition, with complex 2 as a catalyst, α,β-unsaturated carbonyls could be selectively reduced to the corresponding α,β-unsaturated alcohols. The mechanisms of the formation of 2 and the catalytic dehydration process are proposed and partly experimentally verified.
Ren, Shishuai,Xie, Shangqing,Zheng, Tingting,Wang, Yangyang,Xu, Shilu,Xue, Benjing,Li, Xiaoyan,Sun, Hongjian,Fuhr, Olaf,Fenske, Dieter
p. 4352 - 4359
(2018/03/26)

Syntheses of hydrido selenophenolato iron(II) complexes and their catalytic application in hydrosilylation of aldehydes and ketones
Three novel selenophenolato hydrido iron(II) complexes [cis-(H)(SeAr)Fe(PMe3)4] (4–6) (Ar=C6H5 (4), p-MeOC6H4 (5) and o-MeC6H4 (6)) were prepared through the reaction of Fe(PMe3)4 with selenophenols ArSeH (1–3) via Se–H activation. The iron hydrido complexes 4, 5 and 6 could catalyze the hydrosilylation of aldehydes and ketones. Among them complex 5 is the best catalyst for this process. Furthermore, α,β-unsaturated alcohols could be obtained from the selective reduction reactions of the corresponding α,β-unsaturated carbonyls catalyzed by hydrido iron(II) complex 5. This catalytic system has good tolerance for some common groups but it is easy to reduce the nitro group to an amino group. The experiments indicate that the chemoselectivity for this catalytic system is –CHO>–NO2>–C([dbnd]O)CH3. The crystal structure of 6 was determined by X-ray diffraction.
Wang, Yangyang,Ren, Shishuai,Zhang, Wenbo,Xue, Benjing,Qi, Xinghao,Sun, Hongjian,Li, Xiaoyan,Fuhr, Olaf,Fenske, Dieter
p. 1 - 5
(2018/07/06)

Synthesis and catalytic application of [PPP]-pincer iron, nickel and cobalt complexes for the hydrosilylation of aldehydes and ketones
A new synthetic strategy for the novel diphosphine-phosphine oxide ligand (1) (Ph2P-(C6H4))2P(O)H was designed. A series of [PPP]-pincer Fe, Ni, and Co complexes were prepared. All of them were formed by chelate-assisted P-H activation. Two metal hydrides [(Ph2P-(C6H4))2P(O)]Fe(H)(PMe3)2 (2) and [(Ph2P-(C6H4))2P(O)]Ni(H)(PMe3) (3) were obtained at room temperature. The combination of ligand 1 with Co(PMe3)4Me or Co(PMe3)4 afforded the same Co(i) complex [(Ph2P-(C6H4))2P(O)]Co(PMe3)2 (4) via P-H bond activation. The catalytic performance of the Fe, Ni, and Co complexes for the hydrosilylation of aldehydes and ketones was explored. At a catalyst loading of 2 mol%, complex 2 displayed the best catalytic activity for the hydrosilylation by using (EtO)3SiH as the hydrogen source under mild conditions. Complexes 2, 3, and 4 were characterized by spectroscopic methods and X-ray diffraction analysis.
Qi, Xinghao,Zhao, Hua,Sun, Hongjian,Li, Xiaoyan,Fuhr, Olaf,Fenske, Dieter
p. 16583 - 16590
(2018/10/23)

Preparation of hydrido [CNC]-pincer cobalt complexes via selective C-H/C-F bond activation and their catalytic performances
Polyfluorinated aryl imines 2,4,5-R1,R2,R3-C6H2-HC═N-1-C10H7 (R1 = F, R2 = F, R3 = H (1); R1 = F, R2 = H, R3 = F (2) and R1 = F, R2 = F, R3 = F (3)) and F5C6-HC═N-1-C10H7 (7) reacted with CoMe(PMe3)4 to give rise to hydrido [CNC]-pincer cobalt(iii) complexes (2,4,5-R1,R2,R3-C6H-HC═N-1-C10H6)Co(H)(PMe3)2 (R1 = F, R2 = F, R3 = H (4); R1 = F, R2 = H, R3 = F (5); R1 = F, R2 = F, R3 = F (6)) and (F4C6-HC═N-1-C10H6)Co(H)(PMe3)2 (8) via selective C-F/C-H bond activation. Penta-coordinate dicarbonyl cobalt(i) complexes (2,4,5-R1,R2,R3-C6H-HC═N-1-C10H7)Co(CO)2(PMe3) (R1 = F, R2 = H, R3 = F (9); R1 = F, R2 = F, R3 = F (10)) were obtained from reactions of hexa-coordinate cobalt(iii) complexes 5 and 6 with carbon monoxide through reductive elimination. Cobalt(iii) halides (2,4,5-R1,R2,R3-C6H-HC═N-1-C10H6)Co(i)(PMe3)2 (R1 = F, R2 = F, R3 = H (11); R1 = F, R2 = H, R3 = F (12); R1 = F, R2 = F, R3 = F (13)) and (2,4,5-R1,R2,R3-C6H-HC═N-1-C10H6)Co(Br)(PMe3)2 (R1 = F, R2 = F, R3 = H (14); R1 = F, R2 = H, R3 = F (15); R1 = F, R2 = F, R3 = F (16)) were prepared by the interaction between hydrido cobalt(iii) complexes 4-6 and MeI or EtBr. The molecular configurations of complexes 4, 8, and 11 were determined by single crystal X-ray diffraction. We then confirmed that the four hydrido cobalt(iii) complexes 4-6 and 8 could be used as catalysts for reduction of aldehydes and ketones. Complex 8 is the best catalyst among the four complexes and can selectively catalyze the carbonyl groups of α,β-unsaturated aldehydes and ketones.
Yang, Fei,Wang, Yangyang,Lu, Faguan,Xie, Shangqing,Qi, Xinghao,Sun, Hongjian,Li, Xiaoyan,Fuhr, Olaf,Fenske, Dieter
p. 15578 - 15586
(2018/10/04)

Synthesis of Novel Triazole-incorporated Isatin Derivatives as Antifungal, Antitubercular, and Antioxidant Agents and Molecular Docking Study
A library of 1,2,3-triazoles efficiently prepared via click chemistry and evaluated for their antifungal, antitubercular, antioxidant, cytotoxicity, molecular docking and ADME prediction.
Shaikh, Mubarak H.,Subhedar, Dnyaneshwar D.,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Nawale, Laxman,Arkile, Manisha,Sarkar, Dhiman,Shingate, Bapurao B.
supporting information
p. 413 - 421
(2017/02/03)

A Versatile Iridium(III) Metallacycle Catalyst for the Effective Hydrosilylation of Carbonyl and Carboxylic Acid Derivatives
A versatile iridium(III) metallacycle catalysed rapidly and selectively the reduction of a large array of challenging esters and carboxylic acids as well as various ketones and aldehydes. The reactions proceeded in high yields at room temperature by hydrosilylation followed by desilylation. Although the reactions of various aldehydes and ketones resulted exclusively in alcohols, the hydrosilylation of esters led to alcohols or ethers, depending on the type of substrate. Regarding the carboxylic acids, again the nature of the reagent controlled the outcome of the hydrosilylation reaction, either alcohols or aldehydes being formed.
Corre, Yann,Rysak, Vincent,Trivelli, Xavier,Agbossou-Niedercorn, Francine,Michon, Christophe
p. 4820 - 4826
(2017/09/07)

Magnetic nanoparticle-supported DABCO tribromide: A versatile nanocatalyst for the synthesis of quinazolinones and benzimidazoles and protection/deprotection of hydroxyl groups
1,4-Diazabicyclo[2.2.2]octane tribromide supported on magnetic Fe3O4 nanoparticles (MNPs-DABCO tribromide) as a novel heterogeneous tribromide type compound was found to be an efficient and reusable nanocatalyst for the one-pot synthesis of 2-arylquinazolin-4(3H)-ones and 2-aryl-1H-benzo[d]imidazoles through oxidative cyclization of aldehydes with 2-aminobenzamides and 1,2-phenylenediamine, respectively. Also, MNPs-DABCO tribromide catalyzed trimethylsilylation/tetrahydropyranylation and desilylation/depyranylation of a wide variety of alcohols and phenols through changing the solvent medium at room temperature.
Rostami, Amin,Pourshiani, Omid,Navasi, Yahya,Darvishi, Neda,Saadati, Shaghayegh
p. 9033 - 9040
(2017/08/29)

Nano Fe3O4@ZrO2/SO42?: A highly efficient catalyst for the protection and deprotection of hydroxyl groups using HMDS under solvent-free condition
In this work, we introduce a new procedure for the protection and deprotection process of various types of alcohols and phenols by HMDS in the presence of nano magnetic sulfated zirconia (Fe3O4@ZrO2/SO42?) as a solid acid catalyst under very mild and solvent-free condition. This method has interesting advantages like short reaction times and a simple workup process. With regard to some outstanding benefits of this new heterogeneous catalyst such as excellent yield, reusability of the catalyst and easy thermal stability, high acidity, strong and excellent magnetic properties, this method can be very interesting in aspect of green chemistry Principles.
Ghafuri, Hossein,Paravand, Fatemeh,Rashidizadeh, Afsaneh
supporting information
p. 129 - 135
(2016/12/24)

Chemical Properties

Appearance/Colour :White fine crystalline powder
Melting Point: 69-72 °C
Boiling Point: 230 °C at 760 mmHg
Flash Point:95.4 °C
Density: 1.237 g/cm³
Solubility:chloroform: soluble25mg/mL, clear, colorless
Storage Temp.:Store at RT.
Refractive Index: 1.5390 (estimate)
PKA: 13.99±0.10(Predicted)
BRN: 2042182
PSA: 20.23000
LogP: 1.83230

Global suppliers and manufacturers of 17849-38-6total 119 suppliers on LookChem

Company Name
Business Type
Min Order
FOB Price
Main Products
Contact

Wuhan Fortuna Chemical Co.,Ltd
Business Type:Trading Company
Min Order:1 Kilogram
FOB Price:No Data
Main Products:51
Country:

Dayang Chem (Hangzhou) Co.,Ltd.
Business Type:Lab/Research institutions
Min Order:1 Kilogram
FOB Price:USD $ 6.0-6.0 / Kilogram
Main Products:994
Country:

Chemwill Asia Co., Ltd.
Business Type:Manufacturers
Min Order:5 Kiloliter
FOB Price:USD $ 1.2-5.0 / Kiloliter
Main Products:56
Country:

Henan Tianfu Chemical Co., Ltd.
Business Type:Lab/Research institutions
Min Order:1 Kilogram
FOB Price:No Data
Main Products:67
Country:

Zhuozhou Wenxi import and Export Co., Ltd
Business Type:Trading Company
Min Order:1 Kilogram
FOB Price:USD $ 139.0-210.0 / Kilogram
Main Products:1
Country:

Henan Sinotech Import&Export Corporation
Business Type:Other
Min Order:1 Kilogram
FOB Price:USD $ 1.0-1.0 / Kilogram
Main Products:21
Country:

Henan Wentao Chemical Product Co., Ltd.
Business Type:Lab/Research institutions
Min Order:1 Kilogram
FOB Price:USD $ 4.0-5.0 / Kilogram
Main Products:44
Country:

Shanghai Upbio Tech Co.,Ltd
Business Type:Lab/Research institutions
Min Order:1 Kilogram
FOB Price:No Data
Main Products:30
Country:

Baoji Guokang Healthchem co.,ltd
Business Type:Trading Company
Min Order:1 Kilogram
FOB Price:USD $ 42.7-48.3 / Kilogram
Main Products:41
Country:

Qingdao Beluga Import and Export Co., LTD
Business Type:Lab/Research institutions
Min Order:1 Gram
FOB Price:No Data
Main Products:117
Country:

Wuhan Han Sheng New Material Technology Co.，Ltd
Business Type:Trading Company
Min Order:10 Kilogram
FOB Price:No Data
Main Products:58
Country:

Xiamen Hisunny Chemical Co.,Ltd
Business Type:Manufacturers
Min Order:No Data
FOB Price:No Data
Main Products:39
Country:

Hangzhou Keyingchem Co.,Ltd
Business Type:Lab/Research institutions
Min Order:No Data
FOB Price:No Data
Main Products:102
Country:

Hangzhou J&H Chemical Co., Ltd.
Business Type:Lab/Research institutions
Min Order:No Data
FOB Price:No Data
Main Products:46
Country:

Shaanxi Cuicheng Biomedical Technology Co., Ltd.
Business Type:Other
Min Order:1 Gram
FOB Price:No Data
Main Products:30
Country:

Shanghai Massive Chemical Technology Co., Ltd.
Business Type:Lab/Research institutions
Min Order:1 Gram
FOB Price:USD $ 1.0-1.0 / Gram
Main Products:5
Country:

Zibo Hangyu Biotechnology Development Co., Ltd
Business Type:Lab/Research institutions
Min Order:10 Gram
FOB Price:USD $ 100.0-100.0 / Gram
Main Products:313
Country:

SHANGHAI SYSTEAM BIOCHEM CO., LTD
Business Type:Lab/Research institutions
Min Order:100 Gram
FOB Price:USD $ 100.0-2000.0 / Gram
Main Products:24
Country:

HANGZHOU YUNUO CHEMICAL CO.,LTD
Business Type:Trading Company
Min Order:1 Kilogram
FOB Price:No Data
Main Products:83
Country:

TaiChem Taizhou Limited
Business Type:Lab/Research institutions
Min Order:10 Gram
FOB Price:No Data
Main Products:37
Country:

Post a RFQ

Cas No.:

Product Name:

Quantity:

Email:

Company name:

Valid Period:

Detailed Requirements:

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

What can I do for you?
Get Best Price

Get Best Price for 17849-38-6

Article Database

17849-38-6

Articles about 17849-38-6Total 207 be found

More Articles about upstream products of 17849-38-6

More Articles about downstream products of 17849-38-6

Chemical Properties

Appearance/Colour :White fine crystalline powder

Melting Point: 69-72 °C

Boiling Point: 230 °C at 760 mmHg

Flash Point:95.4 °C

Density: 1.237 g/cm³

Solubility:chloroform: soluble25mg/mL, clear, colorless

Storage Temp.:Store at RT.

Refractive Index: 1.5390 (estimate)

PKA: 13.99±0.10(Predicted)

BRN: 2042182

PSA: 20.23000

LogP: 1.83230

Global suppliers and manufacturers of 17849-38-6total 119 suppliers on LookChem

Article Database

17849-38-6

Articles about 17849-38-6Total 207 be found

More Articles about upstream products of 17849-38-6

More Articles about downstream products of 17849-38-6

Chemical Properties

Appearance/Colour :White fine crystalline powder

Melting Point: 69-72 °C

Boiling Point: 230 °C at 760 mmHg

Flash Point:95.4 °C

Density: 1.237 g/cm3

Solubility:chloroform: soluble25mg/mL, clear, colorless

Storage Temp.:Store at RT.

Refractive Index: 1.5390 (estimate)

PKA: 13.99±0.10(Predicted)

BRN: 2042182

PSA: 20.23000

LogP: 1.83230

Global suppliers and manufacturers of 17849-38-6total 119 suppliers on LookChem

Density: 1.237 g/cm³