- Reductive amination of acetals by anilines in the presence of triethylsilane and iodine
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A mild and efficient method for N-alkylation of aromatic amines with various acetals such as aryl, alkyl, cyclic and acyclic acetals was developed. A number of aromatic amines bearing electron-donating or electron-withdrawing substituents were directly alkylated by acetals with excellent yields. The method uses a catalytic amount of I2 and triethylsilane as the hydride source without a metal present. Monoalkylation with excellent chemoselectivity was observed.
- Zhang, Xue-Lin,Yu, Pan,Wu, Yong-Wei,Wu, Qin-Pei,Zhang, Qing-Shan
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- N-alkylation of amines with alcohols catalyzed by a water-soluble cp*iridium complex: An efficient method for the synthesis of amines in aqueous media
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An efficient and environmentally benign catalytic system for the synthesis of various organic amines catalyzed by the water-soluble and air-stable (pentamethylcyclopentadienyl)-iridium-ammine iod- ide complex, [Cp*Ir(NH3)3][I]2 (Cp= pentamethylcyclopentadienyl), has been developed. A wide variety of secondary and tertiary amines were synthesized by the N-alkylation reactions of theoretical equivalents of amines with alcohols in water under air without a base. The synthesis of cyclic amines was also achieved by the N-alkylation of benzylamine with diols. Furthermore, the recycle use of the present water-soluble Cp*Ir catalyst was accomplished. Copyright
- Kawahara, Ryoko,Fujita, Ken-Ichi,Yamaguchi, Ryohei
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- Br?nsted Acid-Catalyzed Transfer Hydrogenation of Imines and Alkenes Using Cyclohexa-1,4-dienes as Dihydrogen Surrogates
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Cyclohexa-1,4-dienes are introduced to Br?nsted acid-catalyzed transfer hydrogenation as an alternative to the widely used Hantzsch dihydropyridines. While these hydrocarbon-based dihydrogen surrogates do offer little advantage over established protocols in imine reduction as well as reductive amination, their use enables the previously unprecedented transfer hydrogenation of structurally and electronically unbiased 1,1-di- and trisubstituted alkenes. The mild procedure requires 5.0 mol % of Tf2NH, but the less acidic sulfonic acids TfOH and TsOH work equally well.
- Chatterjee, Indranil,Oestreich, Martin
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- Sodium borohydride on wet clay: Solvent-free reductive amination of carbonyl compounds using microwaves
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A solvent-flee reductive amination of carbonyl compounds by wet montmorillonite K 10 clay supported sodium borohydride is described; microwave irradiation facilitates the procedure.
- Varma, Rajender S.,Dahiya, Rajender
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- An efficient catalytic reductive amination: A facile one-pot access to 1,2-dihydropyrrolo[3,4-b]indol-3(4H)-ones by using B(C 6 F 5 ) 3 /NaBH 4
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An efficient combination of B(C6F5)3 and NaBH4 was developed for direct reductive amination of aldehydes. A wide range of functional groups such as ester, nitro, nitrile, halogen, alkene, heterocycles were tolerated. Also, acid sensitive protecting groups like TBDMS and TBDPS were not affected. In addition, the present methodology was extended for tandem amination-amidation of 3-formyl-indole-2-carboxylic acids with substituted anilines to afford 1,2-dihydropyrrolo[3,4-b]indol-3(4H)-ones. [Figure not available: see fulltext.]
- Nagarsenkar, Atulya,Prajapti, Santosh Kumar,Babu, Bathini Nagendra
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- A novel one-pot reductive amination of aldehydes and ketones with lithium perchlorate and zirconium borohydride-piperazine complexes
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A novel, one-pot reductive mono-alkylation method of amines (primary and secondary), 1,2-phenylenediamine, O-trimethylsilylhydroxylamine, and N,N-dimethylhydrazine was developed using LiClO4 (5 mol %) as a source for in situ generation of imine
- Heydari, Akbar,Khaksar, Samad,Esfandyari, Maryam,Tajbakhsh, Mahmoud
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- One-pot reductive amination of carbonyl compounds using sodium borohydride-amberlyst 15
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A fast, efficient, and high-yielding method for the preparation of amines by reductive amination of aldehydes and ketones using sodium borohydride in the presence of Amberlyst 15 in tetrahydrofuran and under solvent-free conditions at room temperature is described.
- Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Mahdavi, Nastaran
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- Reactivity of B-Xanthyl N-Heterocyclic Carbene-Boranes
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The synthesis and reactivity of mono- and bis-S-xanthyl NHC-boranes is reported. The new NHC-boranes are prepared through nucleophilic exchange at boron from either mono- or bis-triflyl NHC-boranes, themselves obtained by protolysis of the NHC-BH3/s
- Vallet, Anne-Laure,Telitel, Sofia,Lalevée, Jacques,Lac?te, Emmanuel
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- A novel method for the reduction of imines using the system silane/MoO 2Cl2
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A novel catalytic system, silane/MoO2Cl2 (10 mol %), for the reduction of imines in excellent to moderate yields and chemoselectivity was designed. These results extend the scope of the use of MoO 2Cl2 as an eff
- Fernandes, Ana C.,Rom?o, Carlos C.
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- Conversion of alcohols into N-alkyl anilines via an indirect aza-Wittig reaction
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Iridium catalysed oxidation of alcohols provides the aldehydes required for in situ aza-Wittig reactions and the so-formed imines are reduced to amines under the reaction conditions.
- Cami-Kobeci, Gerta,Williams, Jonathan M. J.
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- 1-Acetyl-2,3-dimethylimidazolidine: A novel organic reductant for transfer hydrogenation
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1-Acetyl-2,3-dimethylimidazolidine was synthesized and was shown to be able to directly reduce a series of aromatic, aliphatic and α,β- unsaturated aldehydes as well as imines in high yields. Georg Thieme Verlag Stuttgart.
- Li, Donghong,Zhang, Yongbin,Zhou, Guofu,Guo, Wei
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- Direct reductive amination of aldehydes catalyzed by carbon nanotube/gold nanohybrids
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Gold digger: The direct reductive amination of aldehydes catalyzed by gold/carbon-nanotube nanohybrids with a silane as a hydride source is reported. Copyright
- Kumar, Rahul,Gravel, Edmond,Hagege, Agnes,Li, Haiyan,Verma, Deepti,Namboothiri, Irishi N. N.,Doris, Eric
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- GaCl3-catalyzed [4+2] annulations of allyltrimethylsilane and trimethyl(propargyl)silane with aldimines
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The GaCl3-catalyzed reaction of allyltrimethylsilane and aldimines gave tetrahydroquinolines in good yields. Similarly, 4-methylquinoline was obtained by using trimethyl(propargyl)silane via a dehydrogenation process.
- Hirashita, Tsunehisa,Kawai, Daisuke,Araki, Shuki
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- Direct Reductive Amination of Aldehydes and Ketones Using Phenylsilane: Catalysis by Dibutyltin Dichloride
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(matrix presented) A procedure for direct reductive amination of aldehydes and ketones was developed which uses phenylsilane as a stoichiometric reductant and dibutyltin dichloride as a catalyst. Suitable amines included anilines and dialkylamines but not monoalkylamines.
- Apodaca, Richard,Xiao, Wei
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- New heteroaromatic azo compounds based on pyridine, isoxazole, and benzothiazole for efficient and highly selective amidation and mono-N-benzylation of amines under Mitsunobu conditions
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4,4′-Azopyridine (2c) is used in conjunction with triphenylphosphine for the efficient conversion of carboxylic acids into amides via Mitsunobu reaction with primary and secondary aliphatic and aromatic amines. The highly selective amidation of only primary aromatic amines with new heterogeneous azo compounds based on benzothiazole 2d and isoxazole 2e is also described. These azo compounds 2c-2e can also be applied for selective mono-N-benzylation of primary aromatic amines. The solid side product heteroaromatic hydrazines obtained under the developed Mitsunobu conditions are easily separated by simple filtration and can be reoxidized to azo compounds for further use.
- Iranpoor, Nasser,Firouzabadi, Habib,Khalili, Dariush
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- Clean and Simple Chemoselective Reduction of Imines to Amines Using Boric Acid-Activated Sodium Borohydride under Solvent-Free Conditions
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The first clean and highly effective solvent-free chemoselective reduction of functionalized aldimines and ketimines bearing easily reducible functional groups, such as ketone, carboxylic acid, ester, nitrile, amide, nitro, furyl and alkenyl groups, to th
- Cho, Byung Tae,Kang, Sang Kyu
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- Metal-free hydrogen activation and hydrogenation of imines by 1,8-bis(dipentafluorophenylboryl)naphthalene
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In the presence of 2,2,6,6-tetramethylpiperidine (TMP) 1,8- bis(dipentafluorophenylboryl)naphthalene has been found to activate H 2 and to hydrogenate various imines under mild conditions.
- Jiang, Chunfang,Blacque, Olivier,Berke, Heinz
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- Metal amidoboranes: Superior double-hydrogen-transfer agents in the reduction of ketones and imines
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Metal amidoboranes (MABs), such as lithium amidoborane (LiAB), show superior ability in reducing ketones and imines directly into their corresponding secondary alcohols and amines, respectively, at room temperature with high conversion and yields. A mechanistic study indicates that the reduction proceeds through a double-hydrogen-transfer process. Both protic H(N) and hydridic H(B) protons in the amidoborane participate in the reaction. Theoretical investigations show that the first (and rate-determining) step of the reduction reaction is the elimination of LiH from LiAB, followed by the transfer of H(Li) to the C site of the unsaturated bond. Copyright
- Xu, Weiliang,Wu, Guotao,Yao, Wei,Fan, Hongjun,Wu, Jishan,Chen, Ping
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- Thiourea-catalyzed transfer hydrogenation of aldimines
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The present letter reports on the thiourea-catalyzed transfer hydrogenation of imines through hydrogen-bonding activation with Hantzsch 1,4-dihydropyridine as the hydrogen source. A variety of aromatic as well as aliphatic aldimines can be reduced to give
- Zhang, Zhiguo,Schreiner, Peter R.
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- Metal-Organic Capsules with NADH Mimics as Switchable Selectivity Regulators for Photocatalytic Transfer Hydrogenation
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Switchable selective hydrogenation among the groups in multifunctional compounds is challenging because selective hydrogenation is of great interest in the synthesis of fine chemicals and pharmaceuticals as a result of the importance of key intermediates. Herein, we report a new approach to highly selectively (>99%) reducing C=X (X = O, N) over the thermodynamically more favorable nitro groups locating the substrate in a metal-organic capsule containing NADH active sites. Within the capsule, the NADH active sites reduce the double bonds via a typical 2e- hydride transfer hydrogenation, and the formed excited-state NAD+ mimics oxidize the reductant via two consecutive 1e- processes to regenerate the NADH active sites under illumination. Outside the capsule, nitro groups are highly selectively reduced through a typical 1e- hydrogenation. By combining photoinduced 1e- transfer regeneration outside the cage, both 1e- and 2e- hydrogenation can be switched controllably by varying the concentrations of the substrates and the redox potential of electron donors. This promising alternative approach, which could proceed under mild reaction conditions and use easy-to-handle hydrogen donors with enhanced high selectivity toward different groups, is based on the localization and differentiation of the 2e- and 1e- hydrogenation pathways inside and outside the capsules, provides a deep comprehension of photocatalytic microscopic reaction processes, and will allow the design and optimization of catalysts. We demonstrate the advantage of this method over typical hydrogenation that involves specific activation via well-modified catalytic sites and present results on the high, well-controlled, and switchable selectivity for the hydrogenation of a variety of substituted and bifunctional aldehydes, ketones, and imines.
- Wei, Jianwei,Zhao, Liang,He, Cheng,Zheng, Sijia,Reek, Joost N. H.,Duan, Chunying
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- Reusable Co-nanoparticles for general and selectiveN-alkylation of amines and ammonia with alcohols
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A general cobalt-catalyzedN-alkylation of amines with alcohols by borrowing hydrogen methodology to prepare different kinds of amines is reported. The optimal catalyst for this transformation is prepared by pyrolysis of a specific templated material, which is generatedin situby mixing cobalt salts, nitrogen ligands and colloidal silica, and subsequent removal of silica. Applying this novel Co-nanoparticle-based material, >100 primary, secondary, and tertiary amines includingN-methylamines and selected drug molecules were conveniently prepared starting from inexpensive and easily accessible alcohols and amines or ammonia.
- Beller, Matthias,Gawande, Manoj B.,Jagadeesh, Rajenahally V.,Kadam, Ravishankar G.,Li, Xinmin,Ma, Zhuang,Petr, Martin,Zbo?il, Radek,Zhou, Bei
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p. 111 - 117
(2022/01/06)
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- Borrowing hydrogen activity of NH2-MIL-125 for N-alkylation of amines with alcohols under solvent and base free condition
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The NH2-MIL-125 showed excellent activity in solvent and base free N-alkylation of amines with alcohols via borrowing hydrogen mechanism. The Ti–O clusters of NH2-MIL-125 provide acidic-basic active sites for the catalysis of reaction. The NH2-MIL-125 was found to be stable and reusable in the reaction.
- Mishra, Manish Kumar,Neogi, Subhadip,Patel, Nisha B.,Shukla, Atindra,Vala, Naresh
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- Study of triaryl-based sulfamic acid derivatives as HPTPβ inhibitors
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A series of novel triaryl-based sulfamic acid analogs was designed, synthesized and evaluated as inhibitors of human protein tyrosine phosphatase beta (HPTPβ). A novel, easy and efficient synthetic method was developed for target compounds, and the activi
- Huang, Guozhi,Li, Song,Wei, Zhao,Xie, Fei,Zhang, Wenjuan,Zheng, Zhibing
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- Cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ
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A cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ is reported, which uses nonmetallic quinone DDQ as an oxidant in the allylation of N-benzylanilines under mild conditions. C–C bond with high selectivity and activity was constructed in this reaction and homoallylic amines were obtained with yields of up to 99%.
- Xiong, Ruimei,Hussain, Muhammad Ijaz,Liu, Qing,Xia, Wen,Xiong, Yan
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supporting information
(2019/12/11)
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- Alkali Metal–Promoted Facile Synthesis of Secondary Amines from Imines and Carbodiimides
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We present here an efficient method for the hydroboration of aldimines (-C=N-) with pinacolborane (HBpin) using an alkali metal catalyst, potassium benzyl. The reaction was accomplished with unprecedented catalytic efficiency under mild and solvent-free conditions to afford the high yield of the corresponding N-boryl amines up to 97percent. Various functionalities on aldimines were incorporated for hydroboration. The corresponding boryl amines were subjected to further hydrolysis to yield the corresponding secondary amines with good yields up to 89percent. This protocol for the reaction demonstrates an atom-economic and green method with diverse imines that bears excellent functional group tolerance. Chemoselective reduction of imines was also attained, with good yields of 74–89percent. We also propose the most plausible mechanism involving the formation of metal hydride as the active pre-catalyst.
- Panda, Tarun K.,Banerjee, Indrani,Sagar, Shweta
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- Catalyst- And solvent-free efficient access to: N -alkylated amines via reductive amination using HBpin
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A sustainable approach which works under catalyst- and solvent-free conditions for the synthesis of structurally diverse secondary amines has been uncovered. This one-pot protocol works efficiently at room temperature and is compatible with a wide range of sterically and electronically diverse aldehydes and primary amines. Notably, this simple process offers scalability, excellent functional group tolerance, chemoselectivity, and is also effective at the synthesis of biologically relevant molecules. This journal is
- Bauri, Somnath,Pandey, Vipin K.,Rit, Arnab
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supporting information
p. 3853 - 3857
(2020/07/27)
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- 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)
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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.
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p. 16507 - 16509
(2020/10/14)
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- Synthesis and Reactivity of Fluorinated Triaryl Aluminum Complexes
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The addition of the Grignard 3,4,5-ArFMgBr to aluminum(III) chloride in ether generates the novel triarylalane Al(3,4,5-ArF)3·OEt2. Attempts to synthesize this alane via transmetalation from the parent borane with trimethylaluminum gave a dimeric structure with bridging methyl groups, a product of partial transmetalation. On the other hand, the novel alane Al(2,3,4-ArF)3 was synthesized from the parent borane and trimethylaluminum. Interestingly, the solid-state structure of Al(2,3,4-ArF)3 shows an extended chain structure resulting from neighboring Al···F contacts. Al(3,4,5-ArF)3·OEt2 was then found to be an effective catalyst for the hydroboration of carbonyls, imines, and alkynes with pinacolborane.
- Ould, Darren M. C.,Carden, Jamie L.,Page, Rowan,Melen, Rebecca L.
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p. 14891 - 14898
(2020/10/02)
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- Ruthenium N-Heterocyclic Carbene Complexes for Chemoselective Reduction of Imines and Reductive Amination of Aldehydes and Ketones
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Chemoselective reduction of imines to secondary amines is catalyzed efficiently by tethered and untethered, half-sandwich ruthenium N-heterocyclic carbene (NHC) complexes at room temperature. The untethered Ru-NHC complexes are more efficient as catalysts for the reduction of aldimines and ketimines than the tethered complexes. Using the best untethered complex as a catalyst, electronic and steric demands on the reaction was probed using a series of imines. Chemoselectivity of the catalyst towards imine reduction was tested by performing inter and intramolecular competitive reactions in a variety of ways. The catalyst exhibits a very high TON and TOF under anaerobic conditions.
- Kathuria, Lakshay,Samuelson, Ashoka G.
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- Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride
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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
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supporting information
p. 162 - 168
(2019/12/11)
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- High-Throughput Screening of Reductive Amination Reactions Using Desorption Electrospray Ionization Mass Spectrometry
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This study describes the latest generation of a high-throughput screening system that is capable of screening thousands of organic reactions in a single day. This system combines a liquid handling robot with desorption electrospray ionization (DESI) mass spectrometry (MS) for a rapid reaction mixture preparation, accelerated synthesis, and automated MS analysis. A total of 3840 unique reductive amination reactions were screened to demonstrate the throughputs that are capable with the system. Products, byproducts, and intermediates were all monitored in full-scan mass spectra, generating a complete view of the reaction progress. Tandem mass spectrometry experiments were conducted to verify the identity of the products formed. The amine and electrophile reactivity trends represented in the data match what is expected from theory, indicating that the system accurately models the reaction performance. The DESI results correlated well with those generated using more traditional mass spectrometry techniques like liquid chromatography-mass spectrometry, validating the data generated by the system.
- Cooks, R. Graham,Ferreira, Christina R.,Li, Yangjie,Logsdon, David L.,Paschoal Sobreira, Tiago Jose,Thompson, David H.
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supporting information
p. 1647 - 1657
(2020/10/26)
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- ROMP-Boranes as Moisture-Tolerant and Recyclable Lewis Acid Organocatalysts
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Although widely used in catalysis, the multistep syntheses and high loadings typically employed are limiting broader implementation of highly active tailor-made arylborane Lewis acids and Lewis pairs. Attempts at developing recyclable systems have thus far met with limited success, as general and versatile platforms are yet to be developed. We demonstrate a novel approach that is based on the excellent control and functional group tolerance of ring-opening metathesis polymerization (ROMP). The ROMP of highly Lewis acidic borane-functionalized phenylnorbornenes afforded both a soluble linear copolymer and a cross-linked organogel. The polymers proved highly efficient as recyclable catalysts in the reductive N-alkylation of arylamines under mild conditions and at exceptionally low catalyst loadings. The modular design presented herein can be readily adapted to other finely tuned triarylboranes, enabling wide applications of ROMP-borane polymers as well-defined supported organocatalysts.
- Vidal, Fernando,McQuade, James,Lalancette, Roger,J?kle, Frieder
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supporting information
p. 14427 - 14431
(2020/10/13)
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- Development of [3]ferrocenophane-derived N/B frustrated Lewis pairs for the metal-free catalytic hydrogenation of imines
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A series of novel [3]ferrocenophane-derived N/B frustrated Lewis pairs (FLPs) were synthesized and successfully applied to the catalytic hydrogenation of imines in 71–93% yields. This approach could be easily conducted on gram scale and provided versatile synthetic route for the key intermediate of sertraline hydrochloride without heavy metal residues.
- Pan, Zhentao,Wang, Hui,Ling, Fei,Xiao, Lian,Song, Dingguo,Zhong, Weihui
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p. 522 - 528
(2019/02/01)
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- 1,4-Dihydropyridine/BF3OEt2 for the reduction of imines: Influences of the amount of added BF3OEt2 and the substitution at N-1 and C-4 of the dihydropyridine ring
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We have evaluated four 1,4-dihydropyridines (DHPs 1a, 1b, 1c and 1d) as reducing agents, which presented free (hydrogenated) or phenyl-substituted N-1 and C-4 positions of the DHP ring. Reactions combining each of the DHP and different amounts of BF3OEt2 were evaluated for the reduction of imine 2a (N-benzylideneaniline). DHP simultaneously substituted at N-1 and C-4 (1a), and DHP substituted at C-4 (1b) gave lower yields for reduction of 2a in comparison with DHPs 1c and 1d (both unsubstituted at the C-4 position). By evaluating the amount of added BF3OEt2 to the reaction mixture, we have found that DHP 1c (substituted at N-1) provided its best yield for amine 3a (82%) when associated with stoichiometric amounts BF3OEt2, while DHP 1d (N-1- and C-4-unsubstituted derivative) was more effective (90% yield) with catalytic quantities of the Lewis acid. The reaction system using DHP 1c under stoichiometric BF3OEt2 could also be successfully applied with additional imine examples and under reductive amination conditions.
- Zattoni, Ingrid F.,Guanaes, Lais D.,Cerqueira, Letícia B.,Pontarolo, Roberto,Ducatti, Diogo R.B.,Duarte, M. Eugênia R.,Noseda, Miguel D.,Trindade, Angela C.L.B.,Gon?alves, Alan G.
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supporting information
(2019/09/12)
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- Borinic Acid Mediated Hydrosilylations: Reductions of Carbonyl Derivatives
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4-Fluoro-2-chlorophenylborinic acid acts as a precatalyst in the presence of phenylsilane for the facile reduction of ketones, aldehydes and imines. Notably, synergistic mediation of a tertiary amine was found essential to trigger silicon to boron hydride transfer to generate a key amine–diarylhydroborane Lewis complex.
- Chardon, Aurélien,Rouden, Jacques,Blanchet, Jér?me
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supporting information
p. 995 - 998
(2018/12/13)
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- Plasma-Made (Ni0.5Cu0.5)Fe2O4 Nanoparticles for Alcohol Amination under Microwave Heating
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Amine N-alkylation is a process involved in the production of a wide range of chemicals. Here we describe the synthesis of well-defined (Ni0.5Cu0.5)Fe2O4 magnetic nanoparticles by plasma induction, and their successful application to amine N-alkylation using alcohols as coupling agents through a borrowing hydrogen pathway. Plasma induction allows precise morphology and size control over nanoparticle synthesis, while allowing the one-pot production of decagram quantities of material. Up to date, such nanoparticles have never been applied for organic reactions. By coupling high-end characterization techniques with catalytic optimization, we showed that small Cu(0) satellite nanoparticles played an essential role in alcohol oxidation, whereas both Ni and Cu were required for the last step of the reaction. Using elemental mapping, we demonstrated that catalyst deactivation occurred through a leaching/re-deposition mechanism of Cu and Ni. The reactions were conducted under microwave conditions, which exerted a positive effect on catalytic activity. Finally, the catalyst was active at low metal loadings (2 mol%) even on the gram-scale, and affording unprecedented TON for this reaction catalyzed by Ni/Cu bimetallic systems (19).
- Li, Alain You,Dumaresq, Nicolas,Segalla, Andréanne,Braidy, Nadi,Moores, Audrey
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p. 3959 - 3972
(2019/08/12)
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- Reduction of imines catalysed by NHC substituted group 6 metal carbonyls
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The catalytic activity of a series of metal carbonyls [M(CO)6], and the corresponding NHC substituted [M(CO)5(NHC)], (M = Cr, Mo, W) complexes was examined in the reduction of N-benzylideneaniline and acetophenone using silyl hydrides and isopropanol/KOH as reductants. The use of various additives and ultraviolet irradiation to promote the reduction of imines using silyl hydrides as reductants was explored. From a comparison of the reactivity of [Mo(CO)6], [Mo(CO)5(NHC)], and [Mo(CO)4(bis NHC)] it was inferred that electron density on the metal centre plays a key role in the catalysis. Four of the best catalysts were then tested in the reduction of a variety of imines with different electronic and steric properties.
- Reshi, Noor U Din,Kathuria, Lakshay,Samuelson, Ashoka G.
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p. 119 - 128
(2018/11/03)
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- Catalyst-Free and Solvent-Free Facile Hydroboration of Imines
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A facile process for the catalyst-free and solvent-free hydroboration of aromatic as well as heteroaromatic imines is reported. This atom-economic methodology is scalable, compatible with sterically and electronically diverse imines, displaying excellent tolerance towards various functional groups, and works efficiently at ambient temperature in most of the cases, affording secondary amines in good to excellent yield after hydrolysis.
- Pandey, Vipin K.,Donthireddy, Siva Nagendra Reddy,Rit, Arnab
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supporting information
p. 3255 - 3258
(2019/09/17)
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- Borrowing Hydrogen-Mediated N-Alkylation Reactions by a Well-Defined Homogeneous Nickel Catalyst
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We report herein a well-defined and bench-stable azo-phenolate ligand-coordinated nickel catalyst which can efficiently execute N-alkylation of a variety of anilines by alcohol. We demonstrate that the redox-active azo ligand can store hydrogen generated during alcohol oxidation and redelivers the same to an in-situ-generated imine bond to result in N-alkylation of amines. The reaction has wide scope, and a large array of alcohols can directly couple to a variety of anilines. Mechanistic studies including deuterium labeling to the substrate establishes the borrowing hydrogen method from alcohols and pinpoints the crucial role of the redox-active azo moiety present on the ligand backbone. Isolation of the ketyl intermediate in its trapped form with a radical quencher and higher kH/kD for the alcohol oxidation step suggest altogether a hydrogen-atom transfer (HAT) to the reduced azo backbone to pave alcohol oxidation as opposed to the conventional metal-ligand bifunctional mechanism. This example clearly demonstrates that an inexpensive base metal catalyst can accomplish an important coupling reaction with the help of a redox-active ligand backbone.
- Bains, Amreen K.,Kundu, Abhishek,Yadav, Sudha,Adhikari, Debashis
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p. 9051 - 9059
(2019/10/02)
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- Band-Gap Narrowing of Highly Stable Heterogeneous ZrO2–ZnO Nanocomposites for the Reductive Amination of Carbonyl Compounds with Formic Acid and Triethylamine
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The band gap of a material can be affected by factors such as size, doping materials, and oxygen vacancies. The decrease in band gap and change in state of ZrO2 with the addition of ZnO indicates interfacial interactions between ZrO2 and ZnO in the nanocomposites (NCs), which is further confirmed by the observed shift of the peaks in the Raman spectra. Heterobimetallic ZrO2–ZnO NCs were synthesized through a sustainable green approach by using sucrose isolated from Angelica gigas Nakai root extract. The highly stable NCs displayed excellent catalytic activity for reductive amination of carbonyl compounds utilizing HCO2H/(CH3CH2)3N as a hydrogen source. The high catalytic performance of the NCs was closely correlated with the narrow band gap and synergistic effect of ZrO2 with ZnO in the NCs.
- Mishra, Kanchan,Kim, Sung Hong,Lee, Yong Rok
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p. 881 - 889
(2019/02/01)
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- Ultrasound-assisted synthesis of UiO-66-NHSO3H via post-synthetic modification as a heterogeneous Br?nsted acid catalyst
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Efficient SO3H-functionalized metal organic framework, UiO-66-NH-SO3H, has been successfully prepared through a post-synthetic modification strategy of UiO-66-NH2 with Chlorosulfonic acid reagent. The UiO-66-NH2 has been synthesized by an ultrasound-assisted (US) method and compared with the conventional-heating method. The UiO-66-NH-SO3H was characterized by elemental analysis, SEM, PXRD and FT-IR to serve as an efficient heterogeneous catalyst for the benzimidazole formation and reductive amination reaction. Furthermore, the UiO-66-NH-SO3H catalyst exhibits good stability, general applicability and excellent recycling performance.
- Homaee, Mahsa,Hamadi, Hosein,Nobakht, Valiollah,Javaherian, Mohammad,Salahshournia, Behrang
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p. 152 - 161
(2019/04/03)
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- PdAu@MIL-100(Fe) cooperatively catalyze tandem reactions between amines and alcohols for efficient N-alkyl amines syntheses under visible light
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PdAu@MIL-100(Fe), with PdAu alloy nanoparticles of ca. 1.7 nm encapsulated inside MIL-100(Fe) cavities, were prepared via a double-solvent impregnation followed by photoreduction. As compared with bare Pd@MIL-100(Fe), bimetallic PdAu@MIL-100(Fe) showed superior activities for the tandem reactions between amines and alcohols to produce N-alkyl amines under visible-light irradiation, ascribed to the promoting effect of metallic Au in the photocatalytic alcohol-to-aldehyde dehydrogenation. A Pd/Au ratio dependent N-alkylation activity was observed over PdAu@MIL-100(Fe), implying the possibility of synchronizing the reaction rates of two consecutive steps in the N-alkylation reaction, i.e., photocatalytic alcohol-to-aldehyde dehydrogenation and imines hydrogenation, to optimize the whole reaction. This study provides a highly efficient and stable catalytic system for the realization of alkylation of amines via a successful coupling of MOF-based photocatalysis and metal nanoparticle-based hydrogenation. This work also demonstrates that the reaction rates of different catalytic steps in a cascade/tandem reaction can be synchronized for an efficient overall reaction via a rational design of the multifunctional catalysts.
- Wang, Dengke,Pan, Yating,Xu, Lizhi,Li, Zhaohui
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p. 248 - 254
(2018/04/02)
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- Cobalt(II) Coordination Polymer as a Precatalyst for Selective Hydroboration of Aldehydes, Ketones, and Imines
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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
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p. 9442 - 9448
(2018/07/05)
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- Well-Defined Amidate-Functionalized N-Heterocyclic Carbene -Supported Rare-Earth Metal Complexes as Catalysts for Efficient Hydroboration of Unactivated Imines and Nitriles
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Four amidate-functionalized N-heterocyclic carbene (NHC) rare-earth metal amido complexes [(κ2-N,O-κ1-L)2REN(SiMe3)2] (L = 1-(C6H5CONCH2CH2)-3-(CH3)3C6H2(N(CH)2NC)) [RE = Er (1), Y (2), Dy (3), Gd (4)] were synthesized by one-pot reactions of 2 equiv of (1-(C6H5CONHCH2CH2)-3-(CH3)3C6H2-(N(CH)2NCH))Br (H2LBr) with 5 equiv of KN(SiMe3)3 followed by treatment with 1 equiv of RECl3 in tetrahydrofuran at -40 °C. These complexes were fully characterized, and their catalytic activities toward hydroboration of unactivated imines and nitriles were investigated, and it was found that these complexes displayed excellent activities as well as remarkable functional group compatibility for imine and nitrile substrates such as halo-, alkyl-, hydroxyl-, N,N-dimethylamino-, and nitro- substituents. Among those, the chemoselectivity for this reaction among the common unsaturated functional groups was achieved in the order CO CN > C=N > CO2Et > CC in the current catalytic system, which may facilitate their further application in synthetic chemistry.
- Huang, Zeming,Wang, Shaowu,Zhu, Xiancui,Yuan, Qingbing,Wei, Yun,Zhou, Shuangliu,Mu, Xiaolong
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p. 15069 - 15078
(2018/12/14)
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- MIL-101(Cr) as a synergistic catalyst for the reduction of imines with trichlorosilane
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The development of catalyst based on porous crystalline materials (PCM) constructed from metal ions or clusters and multidentate organic ligands is a topic of great interest. In view of the Lewis acidic and basic properties of PCMs, we report for the first time that MIL-101(Cr) works as a synergistic catalyst for the reduction of imines with trichlorosilane as the hydrogen source. Both ketimines and aldimines were tolerated with this protocol, giving the corresponding amines in moderate to high yields. The operational simplicity as well as mild reaction conditions renders this protocol an attractive approach for the synthesis of amines. Furthermore, a chiral MOF, CMIL-101, was also realized by grafting chiral N-formyl proline derivatives to the open metal sites. Moreover, CMIL-101 exhibited a comparable catalytic performance with its homogeneous counterpart in terms of yields and enantioselectivities.
- Chen, Jingwen,Chen, Xiaoling,Zhang, Zhiguo,Bao, Zongbi,Xing, Huabin,Yang, Qiwei,Ren, Qilong
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p. 163 - 169
(2018/01/05)
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- Unmodified Fe3O4 nanostructure promoted with external magnetic field: safe, magnetically recoverable, and efficient nanocatalyst for N- and C-alkylation reactions in green conditions
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Transition metal compounds have emerged as suitable catalysts for organic reactions. Magnetic compounds as soft Lewis acids can be used as catalysts for organic reactions. In this report, the Fe3O4 nanostructures were obtained from Fe2+ and Fe3+-salts, under an external magnetic field (EMF) without any protective agent. The X-ray photoelectron spectroscopy, scanning electron microscopy, and energy dispersive X-ray spectroscopy tools were used to characterize these magnetic compounds. The two-dimensional (2-D, it showed nanometric size in the two dimensions, nanorod structure) Fe3O4 compound showed high catalytic activity and stability in N- and C-alkylation reactions. A diverse range of N- and C-alkylation products were obtained in moderate to high yield under green and mild conditions in air. Also the N- and C-alkylation products can be obtained with different selectivity and yield by exposure reactions with EMF. Results of alkylation reactions showed that the presence of Fe(II) and Fe(III) species on the surface of magnetic catalysts (phase structure of magnetic compounds) are essential as very cheap active sites. Also, morphology of magnetic catalysts had influence on their catalytic performances. After the reaction, the catalyst/product(s) separation could be easily achieved with an external magnet and more than 95% of catalyst could be recovered. The catalyst was reused at least four times without any loss of its high catalytic activity for N- and C-alkylation reactions.
- Rafiee, Ezzat,Joshaghani, Mohammad,Abadi, Parvaneh Ghaderi-Shekhi
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p. 2503 - 2522
(2018/01/04)
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- Main-Group-Catalyzed Reductive Alkylation of Multiply Substituted Amines with Aldehydes Using H2
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Given the growing demand for green and sustainable chemical processes, the catalytic reductive alkylation of amines with main-group catalysts of low toxicity and molecular hydrogen as the reductant would be an ideal method to functionalize amines. However, such a process remains challenging. Herein, a novel reductive alkylation system using H2 is presented, which proceeds via a tandem reaction that involves the B(2,6-Cl2C6H3)(p-HC6F4)2-catalyzed formation of an imine and the subsequent hydrogenation of this imine catalyzed by a frustrated Lewis pair (FLP). This reductive alkylation reaction generates H2O as the sole byproduct and directly functionalizes amines that bear a remarkably wide range of substituents including carboxyl, hydroxyl, additional amino, primary amide, and primary sulfonamide groups. The synthesis of isoindolinones and aminophthalic anhydrides has also been achieved by a one-pot process that consists of a combination of the present reductive alkylation with an intramolecular amidation and intramolecular dehydration reactions, respectively. The reaction showed a zeroth-order and a first-order dependence on the concentration of an imine intermediate and B(2,6-Cl2C6H3)(p-HC6F4)2, respectively. In addition, the reaction progress was significantly affected by the concentration of H2. These results suggest a possible mechanism in which the heterolysis of H2 is facilitated by the FLP comprising THF and B(2,6-Cl2C6H3)(p-HC6F4)2.
- Hoshimoto, Yoichi,Kinoshita, Takuya,Hazra, Sunit,Ohashi, Masato,Ogoshi, Sensuke
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supporting information
p. 7292 - 7300
(2018/06/01)
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- Ansa-ferrocene derived tertiary amine, and preparation method and application thereof
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The invention discloses ansa-ferrocene derived tertiary amine, and a preparation method and application thereof. The application is particularly as follows: the ansa-ferrocene derived tertiary amine and tri(pentafluorphenyl)boron according to the ratio of
- -
-
Paragraph 0040
(2017/10/13)
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- Transition metal free catalytic hydroboration of aldehydes and aldimines by amidinato silane
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The transition metal free catalytic hydroboration of aldehydes and ketones is very limited and has not been reported with a well-defined silicon(iv) compound. Therefore, we chose to evaluate the previously reported silicon(iv) hydride [PhC(NtBu)2SiHCl2], (1) as a single component catalyst and found that it catalyzes the reductive hydroboration of a range of aldehydes with pinacolborane (HBpin) under ambient conditions. In addition, compound 1 can catalyze imine hydroboration. DFT calculation was carried out to understand the mechanism.
- Bisai, Milan Kumar,Pahar, Sanjukta,Das, Tamal,Vanka, Kumar,Sen, Sakya S.
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p. 2420 - 2424
(2017/03/08)
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- (η5-Pentamethylcyclopentadienyl)iridium Complex Catalyzed Imine Reductions Utilizing the Biomimetic 1,4-NAD(P)H Cofactor and N-Benzyl-1,4-dihydronicotinamide as the Hydride-Transfer Agent
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The interaction between synthetic organometallic complexes and metabolic cofactors has proven to be a newly emerging topic in bioorganometallic chemistry. Thus, the first cationic Cp*Ir-catalyzed (Cp=η5-pentamethylcyclopentadienyl) imine reduction in neutral buffered aqueous medium was examined. The reaction was found to proceed through hydride transfer from NADH as the hydride source at room temperature in air. Cationic Cp*Ir complexes proved to be the most efficient catalysts for this transformation. We also highlighted that the choice of the proton source was essential. The method was subsequently applied to cyclic and noncyclic imines. Eventually, the concept was extended to the reductive alkylation of one amine.
- Soetens, Mathieu,Drouet, Fleur,Riant, Olivier
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p. 929 - 933
(2017/03/27)
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- One-pot Reductive Amination of Carbonyl Compounds with NaBH4-B(OSO3H)3/SiO2 in Acetonitrile and in Solvent-free Condition
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An efficient one-pot procedure for the direct reductive amination of aldehyde and ketones was achieved in the presence of sodium borohydride by using B(OSO3H)3/SiO2(SBSA) as the reusable solid catalyst in acetonitrile and solvent-free conditions. Both aromatic and aliphatic aldehyde reacted well to give the corresponding amines in excellent yields. All the products are known and well-characterized. The catalyst is recoverable and could be easily recycled by filtration and reused several times without any significant loss of its activity. SBSA acts as a dual Br?nsted/Lewis acid that is an air-stable and cost-effective solid acid. [Figure not available: see fulltext.]
- Hamadi, Hosein,Javadi, Samira
-
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- Discovery of 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-phenylacetamide derivatives as new potent and selective human sirtuin 2 inhibitors
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Human sirtuin 2 (SIRT2) plays pivotal roles in multiple biological processes such as cell cycle regulation, autophagy, immune and inflammatory responses. Dysregulation of SIRT2 was considered as a main aspect contributing to several human diseases, including cancer. Development of new potent and selective SIRT2 inhibitors is currently desirable, which may provide a new strategy for treatment of related diseases. Herein, a structure-based optimization approach led to new 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-phenylacetamide derivatives as SIRT2 inhibitors. SAR analyses with new synthesized derivatives revealed a number of new potent SIRT2 inhibitors, among which 28e is the most potent inhibitor with an IC50 value of 42?nM. The selectivity analyses found that 28e has a very good selectivity to SIRT2 over SIRT1 and SIRT3. In cellular assays, 28e showed a potent ability to inhibit human breast cancer cell line MCF-7 and increase the acetylation of α-tubulin in a dose-dependent manner. This study will aid further efforts to develop highly potent and selective SIRT2 inhibitors for the treatment of cancer and other related diseases.
- Yang, Lingling,Ma, Xiaobo,Yuan, Chen,He, Yanying,Li, Ling,Fang, Sha,Xia, Wei,He, Tao,Qian, Shan,Xu, Zhihong,Li, Guobo,Wang, Zhouyu
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p. 230 - 241
(2017/04/19)
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- N-(4-substituted phenyl)-2-substituted acetamide compound and is use as SIRT2 protein inhibitor
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The invention discloses a compound shown in the formula I or its pharmaceutically acceptable salt, crystalline form and solvate. X represents a group shown in the description, Y represents a group shown in the description, R1, R2 and R3 independently represent H, hydroxyl, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl or phenyl, and R4 represents aryl, heteroaryl, substituted aryl or substituted heteroaryl. The novel compound shown in the formula I has good inhibition activity to SIRT2 and tumors, has a good medicinal value and provides a novel potential choice for clinical medication.
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-
Paragraph 0167; 0168
(2017/08/02)
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- A Rapid and Additive-Free Ruthenium-Catalyzed Reductive Amination of Aromatic Aldehydes
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The ruthenium complex [(η6-cymene)Ru(Cl)(dpmpy)]+{dpmpy = 2-[2-(dimethylamino)pyrimidin-4-yl]pyridine} is highly reactive in catalyzing the reductive amination of aromatic aldehydes through in situ generated imines with 2-propanol as the hydrogen source following a transfer-hydrogenation mechanism. This transformation does not require any activating additives and is applicable to a broad variety of aldehydes.
- Kerner, Christian,Straub, Sascha-Dominic,Sun,Thiel, Werner R.
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supporting information
p. 3060 - 3064
(2016/07/12)
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- Molecular Coordination-Switch in a New Role: Controlling Highly Selective Catalytic Hydrogenation with Switchability Function
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A molecular coordination-switch controlled by acid-base input has been developed and utilized in switchable catalysis. The molecular switch consists of a hybrid pyridylidene-benzimidazole ligand bound to an IrIIICp? moiety wherein the benzimidazole functionality has been utilized for acid/base controlled reversible coordination, switching between an IrIII-benzimidazole species (form I; neutral imino-type N-coordination) and an IrIII-benzimidazolate species (form II; anionic amido-type N-Ir bonding). Owing to the distinctly different nature of the metal-ligand bonding, it has been demonstrated that while the form I is almost inactive (TOF 1 h-1) in catalytic hydrogenation of imine under ambient pressure and temperature, the form II is greater than an order of magnitude more efficient (TOF 15.8 h-1) in the same catalysis. Moreover, the catalysis could be switched OFF and ON efficiently for several cycles with the addition of acid and base, respectively. Spectroscopic studies and kinetics have been performed to understand the switching activity.
- Semwal, Shrivats,Choudhury, Joyanta
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p. 2424 - 2428
(2016/04/26)
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- One-pot reductive amination of araldehydes by aniline using borohydride with CeCl3·7H2O as catalyst
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A one-pot, two-step reductive amination of araldehydes or acetophenones with anilines using NaBH4as a cheap hydride source and catalysed by CeCl3·7H2O has been achieved in EtOH at room temperature in good yields.
- Zhu, Xun,Zhou, Xiuqin,Zhang, Wei
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p. 390 - 393
(2015/08/18)
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- Metal-free reductive amination of aldehydes for the synthesis of secondary and tertiary amines
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Reductive amination of aldehydes to produce secondary amines at room-temperature by in situ generated benzimidazoline is discussed. The bonus of the reaction is the formation of pharmaceutically important benzimidazole as a by-product in good yield, which can be recovered from the reaction mixture by simple filtration. The product, secondary amine, is transformed to tertiary amine in the same pot.
- Ambica,Khajuria, Rajni,Saini, Yeshwinder,Kapoor, Kamal K
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p. 1252 - 1259
(2015/11/25)
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- Preparation of arylamines form aldehydes by Zn(BH4)2/MgBr2
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Reductive aminationa varietyof aldehydes with different anilines has been performed by Zn(BH4)2/MgBr2as reducing system in THF at room temperature in high to excellent yields of the corresponding secondary amines (80-90%).
- Mahmoudi, Mina,Setamdideh, Davood
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p. 1215 - 1218
(2015/10/28)
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- ANTI-VIRAL COMPOUNDS
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Compounds effective in inhibiting replication of Hepatitis C virus (“HCV”) are described. This invention also relates to processes of making such compounds, compositions comprising such compounds, and methods of using such compounds to treat HCV infection.
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Paragraph 0216; 0217
(2015/11/24)
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- Base-promoted N-alkylation using formamides as the N-sources in neat water
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An efficient catalyst-free, alternative method for the C-N bond formation reaction of alkyl electrophiles using formamides as the N-sources was achieved under mild conditions. The reaction possesses the advantages of a broad range of substrates scope and wide functional group tolerance. It should also be noted that this process was performed using the environmentally benign water as the sole solvent, and high yield can also be achieved in ten-gram scale.
- Chen, Wen-Xin,Zhang, Cai-Yun,Shao, Li-Xiong
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p. 880 - 885
(2014/01/23)
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- Metal-free reduction of secondary and tertiary N-phenyl amides by tris(pentafluorophenyl)boron-catalyzed hydrosilylation
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Tris(pentafluorophenyl)boron B(C6F5)3 is an effective catalyst for the hydrosilylative reduction of tertiary and N-phenyl secondary amides. It allows for the mild reduction of a variety of these amides in near quantitative yield, with minimal purification, at low temperatures, and with short reaction times. This reduction shows functional group tolerance for alkenes, nitro groups, and aryl halides, including aryl iodides.
- Chadwick, Ryan C.,Kardelis, Vladimir,Lim, Philip,Adronov, Alex
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p. 7728 - 7733
(2014/09/30)
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- Ionic liquid coated sulfonated carbon/silica composites: Novel heterogeneous catalysts for organic syntheses in water
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Ionic liquid coated sulfonic acid functionalized amorphous carbon/silica composites derived from a starch-glucose mixture were developed and their catalytic activities were evaluated for Knoevenagel condensation, reductive amination of aldehydes and ketones, and for Michael addition of indole to α,β-unsaturated ketones in aqueous medium. The catalyst prepared from starch-glucose mixture (3:1) [CSC-Star-Glu-IL2] showed the highest activity in water. The catalysts were characterized by FTIR, TGA, elemental analysis, and the most active was further characterized by XRD, SEM and TEM.
- Gupta, Princy,Kour, Manmeet,Paul, Satya,Clark, James H.
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p. 7461 - 7470
(2014/02/14)
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- Zwitterionic-surfactant-stabilized palladium nanoparticles as catalysts in the hydrogen transfer reductive amination of benzaldehydes
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Palladium nanoparticles (NPs) stabilized by a zwitterionic surfactant are revealed here to be good catalysts for the reductive amination of benzaldehydes using formate salts as hydrogen donors in aqueous isopropanol. In terms of environmental impact and e
- Drinkel, Emma E.,Campedelli, Roberta R.,Manfredi, Alex M.,Fiedler, Haidi D.,Nome, Faruk
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p. 2574 - 2579
(2014/04/17)
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- N-Alkylation of amines with alcohols over nanosized zeolite beta
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Direct N-alkylation of amines with alcohols was successfully performed by using nanosized zeolite beta, which showed the highest catalytic activity among other conventional zeolites. This method has several advantages, such as eco-friendliness, moderate to high yields, and simple work-up procedure. The catalyst was successfully recovered and reused without significant loss of activity and only water is produced as co-product. In addition, imines were also efficiently prepared from the tandem reactions of amines with 2-, 3- and 4-nitrobenzyl alcohols using nanosized zeolite beta.
- Reddy, Marri Mahender,Kumar, Macharla Arun,Swamy, Peraka,Naresh, Mameda,Srujana, Kodumuri,Satyanarayana, Lanka,Venugopal, Akula,Narender, Nama
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supporting information
p. 3474 - 3483
(2013/12/04)
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- Fast and efficient reductive amination of aldehydes by NaBH 4/B(OH)3 and NaBH4/Al(OH)3
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Reductive amination a variety of aldehydes and anilines to their corresponding secondary amines were carried out with NaBH4/B(OH) 3 and NaBH4/Al(OH)3 as new reducing systems in CH3CN at room temperature in high to excellent yields of products (90-96%).
- Setamdideh, Davood,Hasani, Samira,Noori, Shahla
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p. 1267 - 1271
(2014/04/03)
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