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A new porous Co(ii)-metal-organic framework for high sorption selectivity and affinity to CO2and efficient catalytic oxidation of benzyl alcohols to benzaldehydes
Herein, we report a new 3D porous Co(ii)-based metal-organic framework catalyst (Me2NH2)2[Co3(L)2(H2O)2]·2DMF (MOF I), which has been successfully prepared by using Co(ii) ions and rigid V-shaped 3,5-di(2,4-dicarboxylphenyl)pyridine (H4L) via the solvothermal reaction. Structural analysis reveals that I displays a porous structure with the pore size of 16.2 × 7.2 ?2 based on the trinuclear [Co3(COO)4(H2O)2N2] secondary building units (SBUs). Gas sorption experiments on the guest free sample I′ reveals a high capacity and selectivity to CO2 over CH4. And further, the catalytic explorations of the I′-catalyzed system (I′: 3 mol%; proline: 40 mol%; CH3CN: 2 mL) reveal that benzyl alcohols with different structures can be efficiently transformed into benzyl alcohols without by-products under mild conditions.
Wu, Yun-Long,Yang, Rong-Rong,Yang, Guo-Ping,Yan, Yang-Tian,Su, Xiao-Lei,He, Xin-Hai,Song, Yan-Yan,Ma, Zheng-Sheng,Wang, Yao-Yu
p. 3717 - 3723
(2021/05/31)

Homogeneous CuCl2/TMEDA/TEMPO-Catalyzed chemoselective base- and halogen- free aerobic oxidation of primary alcohols in mild conditions
This article describes the developing of a base- and halogen- free homogeneous system aiming to chemoselectively oxidize allyl, furyl, aryl and heteroaryl primary alcohols. The current easy-to-handle aerobic system uses few amounts of CuCl2/TMEDA/TEMPO system under mild reaction conditions to produce aldehydes in high yields. Moreover, the CuCl2/TMEDA cyclic voltammetry was measured for the first time, disclosing that TMEDA as ligand substantially affects the redox potential (E1/2) of the couple E1/2Cu2+/Cu+ to E1/2Cu2+/Cu+-TMEDA by 454 mV in the redox system.
Alves, Otávio A. L.,Chagas, Rafael C. R.,Princival, Jefferson L.,Ribeiro, RogérioT.,Silva, Emmanuel D.,Villar, José A. F. P.
(2021/08/03)

4CzIPN catalyzed photochemical oxidation of benzylic alcohols
A green photoredox oxidation of benzylic primary and secondary alcohols to aldehydes and ketones with air as an oxidant was reported. The oxidation shows broad substrate scope and excellent selectivity over benzylic alcohols to the aliphatic alcohols. Further mechanistic studies revealed a quinuclidine mediated HAT process, and blue LEDs promoted 4CzlPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene) photoredox cycle were involved in our oxidation.
Zhang, Heng,Guo, Tianyun,Wu, Mingzhong,Huo, Xing,Tang, Shouchu,Wang, Xiaolei,Liu, Jian
supporting information

(2021/02/20)

A Magnetically Recyclable Palladium-Catalyzed Formylation of Aryl Iodides with Formic Acid as CO Source: A Practical Access to Aromatic Aldehydes
A magnetically recyclable palladium-catalyzed formylation of aryl iodides under CO gas-free conditions has been developed by using a bidentate phosphine ligand-modified magnetic nanoparticles-anchored- palladium(II) complex [2P-Fe 3O 4@SiO 2-Pd(OAc) 2] as catalyst, yielding a wide variety of aromatic aldehydes in moderate to excellent yields. Here, formic acid was employed as both the CO source and the hydrogen donor with iodine and PPh 3as the activators. This immobilized palladium catalyst can be obtained via a simple preparative procedure and can be facilely recovered simply by using an external magnetic field, and reused at least 9 times without any apparent loss of catalytic activity.
You, Shengyong,Zhang, Rongli,Cai, Mingzhong
p. 1962 - 1970
(2021/01/25)

Palladium-Catalyzed Reductive Carbonylation of (Hetero) Aryl Halides and Triflates Using Cobalt Carbonyl as CO Source
An efficient protocol for the reductive carbonylation of (hetero) aryl halides and triflates under CO gas-free conditions using Pd/Co2(CO)8 and triethylsilane has been developed. The mild reaction conditions, enhanced chemoselectivity and, easy access to heterocyclic and vinyl carboxaldehydes highlights its importance in organic synthesis.
Dogga, Bhushanarao,Joseph, Jayan T.,Kumar, C. S. Ananda
p. 309 - 313
(2020/12/23)

One-Pot Direct Oxidation of Primary Amines to Carboxylic Acids through Tandem ortho-Naphthoquinone-Catalyzed and TBHP-Promoted Oxidation Sequence
Biomimetic oxidation of primary amines to carboxylic acids has been developed where the copper-containing amine oxidase (CuAO)-like o-NQ-catalyzed aerobic oxidation was combined with the aldehyde dehydrogenase (ALDH)-like TBHP-mediated imine oxidation protocol. Notably, the current tandem oxidation strategy provides a new mechanistic insight into the imine intermediate and the seemingly simple TBHP-mediated oxidation pathways of imines. The developed metal-free amine oxidation protocol allows the use of molecular oxygen and TBHP, safe forms of oxidant that may appeal to the industrial application.
Kim, Hun Young,Oh, Kyungsoo,Si, Tengda
supporting information
p. 18150 - 18155
(2021/12/09)

Radical induced disproportionation of alcohols assisted by iodide under acidic conditions
The disproportionation of alcohols without an additional reductant and oxidant to simultaneously form alkanes and aldehydes/ketones represents an atom-economical transformation. However, only limited methodologies have been reported, and they suffer from a narrow substrate scope or harsh reaction conditions. Herein, we report that alcohol disproportionation can proceed with high efficiency catalyzed by iodide under acidic conditions. This method exhibits high functional group tolerance including aryl alcohol derivatives with both electron-withdrawing and electron-donating groups, furan ring alcohol derivatives, allyl alcohol derivatives, and dihydric alcohols. Under the optimized reaction conditions, a 49% yield of 5-methyl furfural and a 49% yield of 2,5-diformylfuran were obtained simultaneously from 5-hydroxymethylfurfural. An initial mechanistic study suggested that the hydrogen transfer during this redox disproportionation occurred through the inter-transformation of HI and I2. Radical intermediates were involved during this reaction.
Huang, Yang,Jiang, Haiwei,Li, Teng,Peng, Yang,Rong, Nianxin,Shi, Hexian,Yang, Weiran
supporting information
p. 8108 - 8115
(2021/10/29)

Synthesis of silyl formates, formamides, and aldehydesviasolvent-free organocatalytic hydrosilylation of CO2
Carbon dioxide (CO2) was used as a C1 source to prepare silyl formates, formamides, and aldehydes. Tetrabutylammonium acetate (TBAA) catalyzed the solvent-freeN-formylation of amines with CO2and hydrosilane to give formamides including Weinreb formamide, Me(MeO)NCHO, which was successively converted into aldehydes by one-pot reactions with Grignard reagents.
Ema, Tadashi,Hasegawa, Jun-Ya,Hiyoshi, Mahoko,Murata, Takumi,Ratanasak, Manussada
supporting information
p. 5783 - 5786
(2020/06/03)

Selective oxidation of alcohols by porphyrin-based porous polymer-supported manganese heterogeneous catalysts
A series of porphyrin-based porous polymers to support Mn heterogeneous catalysts (Mn/TFP-DPM, Mn/TFP-DPM-2, Mn/TFP-DPM-3, and Mn/TFP-DPM-4) in the selective oxidation of alcohols were designed. TFP-DPM and TFP-DPM-2 demonstrated micro/nanoscale spherical morphology, whereas TFP-DPM-3 and TFP-DPM-4 exhibited nanosheets structure. According to surface area and porosity analysis results, the specific surface areas of these catalysts were less than 300 m2 g–1. Thermogravimetric analysis indicated that the synthesized catalysts maintain their stability even at 300 °C. Catalysts Mn/TFP-DPM and Mn/TFP-DPM-3, which had the smallest and largest specific surface area among the four catalysts, respectively, were used to perform selective oxidation reaction of alcohols, with experimental results indicating that both have excellent catalytic performance. As these catalysts possess good catalytic performance despite their low specific surface area, we suggest that porphyrin-based porous polymer-supported Mn heterogeneous catalysts are promising materials for selective oxidation of alcohols.
Chen, Jian,Zhang, Yan,Zhu, Dajian,Li, Tao
(2019/12/24)

Mechanistic insight into concerted proton-electron transfer of a Ru(IV)-oxo complex: A possible oxidative asynchronicity
We have thoroughly investigated the oxidation of benzyl alcohol (BA) derivatives by a RuIV(O) complex (RuIV(O)) in the absence or presence of Br?nsted acids in order to elucidate the proton-coupled electron-transfer (PCET) mechanisms in C-H oxidation on the basis of a kinetic analysis. Oxidation of BA derivatives by RuIV(O) without acids proceeded through concerted proton-electron transfer (CPET) with a large kinetic isotope effect (KIE). In contrast, the oxidation of 3,4,5-trimethoxy- BA ((MeO)3-BA) by RuIV(O) was accelerated by the addition of acids, in which the KIE value reached 1.1 with TFA (550 mM), indicating an alteration of the PCET mechanism from CPET to stepwise electron transfer (ET) followed by proton transfer (PT). Although the oxidized products of BA derivatives were confirmed to be the corresponding benzaldehydes in the range of acid concentrations (0-550 mM), a one-electron-reduction potential of RuIV(O) was positively shifted with increases in the concentrations of acids. The elevated reduction potential of RuIV(O) strongly influenced the PCET mechanisms in the oxidation of (MeO)3-BA, changing the mechanism from CPET to ET/PT, as evidenced by the driving-force dependence of logarithms of reaction rate constants in light of the Marcus theory of ET. In addition, dependence of activation parameters on acid concentrations suggested that an oxidative asynchronous CPET, which is not an admixture of the CPET and ET/PT mechanisms, is probably operative in the boundary region (0 mM [TFA] 50 mM) involving a one-protoninteracted RuIV(O) H+ as a dominant reactive species.
Kojima, Takahiko,Kotani, Hiroaki,Shimomura, Hinatsu,Ikeda, Kei,Ishizuka, Tomoya,Shiota, Yoshihito,Yoshizawa, Kazunari
p. 16982 - 16989
(2020/11/09)

Utilizing a copper-free Sonogashira reaction in the synthesis of the leukotriene a4 hydrolase modulator batatasin IV
Batatasin IV is a dihydrostilbenoid isolated from Chinese yams which was shown to have inhibitory activities against plant growth. Later studies showed that this compound may exhibit anti-inflammatory properties by inhibiting the epoxide hydrolase activity of the leukotriene A4 hydrolase enzyme. To access the dihydrostilbenoid skeleton, a copper-free SPhos-mediated Sonogashira reaction was conceived and the substrate scope was explored. Our results indicate that the reaction can tolerate the presence of free alcohols, aldehydes, nitro groups, and anilinyl groups. However, a substituent with an acidic phenol or carboxylic acid group gave significantly lower yields. Next, a total synthesis of batatasin IV was accomplished in 16% overall yield incorporating the reported copper-free Sonogashira reaction. Finally, we show that batatasin IV inhibits the hydrolysis of alanine p-nitroanilide by leukotriene A4 hydrolase with an IC50 of 91.4 μM.
Petruncio, Greg,Girgis, Michael,Moummi, Sanae,Jayatilake, Meth,Lee, Kyung Hyeon,Paige, Mikell
supporting information

(2020/10/27)

Photochemical α-cleavage reaction of 3’,5’-dimethoxybenzoin: A combined time-resolved spectroscopy and computational chemistry study
Benzoin is one of the most commonly used photoinitiators to induce free radical polymerization. Here, improved benzoin properties could be accomplished by the introduction of two methoxy substituents, leading to the formation of 3’,5’-dimethoxybenzoin (DMB) which has a higher photo-cleavage quantum yield (0.54) than benzoin (0.35). To elucidate the underlying reaction mechanisms of DMB and obtain direct information of the transient species involved, femtosecond transient absorption (fs-TA) and nanosecond transient absorption (ns-TA) spectroscopic experiments in conjunction with density functional theory/time-dependent density functional theory (DFT/TD-DFT) calculations were performed. It was found that the photo-induced α-cleavage (Norrish Type I reaction) of DMB occurred from the nπ* triplet state after a rapid intersystem crossing (ISC) process (7.6 ps), leading to the generation of phenyl radicals on the picosecond time scale. Compared with Benzoin, DMB possesses two methoxy groups which are able to stabilize the alcohol radical and thus result in a stronger driving force for cleavage and a higher quantum yield of photodissociation. Two stable conformations (cis-DMB and trans-DMB) at ground state were found via DFT calculations. The influence of the intramolecular hydrogen bond on the α-cleavage of DMB was elaborated.
Du, Lili,Li, Yuanchun,Phillips, David Lee,Tang, Wenjian,Yan, Zhiping,Zhang, Xiting
supporting information

(2020/08/28)

Visible-light assisted of nano Ni/g-C3N4 with efficient photocatalytic activity and stability for selective aerobic C?H activation and epoxidation
A selective, economical, and ecological protocol has been described for the oxidation of methyl arenes and their analogs to the corresponding carbonyl compounds and epoxidation reactions of alkenes with molecular oxygen (O2) or air as a green oxygen source, under mild reaction conditions. The nano Ni/g-C3N4 exhibited high photocatalytic activity, stability, and selectivity in the C?H activation of methyl arenes, methylene arenes, and epoxidation of various alkenes under visible- light irradiation without the use of an oxidizing agent and under base free conditions.
Akrami, Zahra,Hosseini-Sarvari, Mona
supporting information

(2020/10/13)

A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO2F2/K2CO3 Using DMSO as Solvent and Oxidant
A practical, general and mild oxidation of primary and secondary alcohols to carbonyl compounds proceeds in yields of up to 99% using SO2F2 as electrophile in DMSO as both the oxidant and the solvent at ambient temperature. No moisture- and oxygen-free conditions are required. Stoichiometric amount of inexpensive K2CO3, which generates easy to separate by-products, is used as the base. Thus, 5-gram scale runs proceeded in nearly quantitative yields by a simple filtration as the work-up. The use of a polar solvent such as DMSO, which usually promotes competing Pummerer rearrangement, is also noteworthy. This protocol is compatible with a variety of common N-, O-, and S-functional groups on (hetero)arene, alkene and alkyne substrates (68 examples). The protocol was applied (99% yield) to a formal synthesis of the important cholesterol-lowering drug Rosuvastatin. (Figure presented.).
Zha, Gao-Feng,Fang, Wan-Yin,Leng, Jing,Qin, Hua-Li
supporting information
p. 2262 - 2267
(2019/04/17)

Selective Aerobic Oxidation of Benzylic Alcohols Catalyzed by a Dicyclopropenylidene-Ag(I) Complex
The unprecedented synthesis, single-crystal X-ray structure, and first catalytic application of a dicarbene-Ag(I) complex [Ag(BAC)2][CO2CF3] (BAC = bis(diisopropyl)aminocyclopropenylidene) is reported. This novel complex provides a versatile catalytic platform for selective aerobic oxidation of benzylic alcohols to aldehyde or ketone products in high yields. Ease of experimental execution coupled with the use of abundant atmospheric molecular oxygen as an oxidant and low catalyst loading are inherit strengths of these oxidations.
Mir, Roya,Rowshanpour, Rozhin,Dempsey, Katie,Pilkington, Melanie,Dudding, Travis
p. 5726 - 5731
(2019/05/10)

Ruthenium(ii)-catalyzed electrooxidative [4+2] annulation of benzylic alcohols with internal alkynes: Entry to isocoumarins
A new ruthenium(ii)-catalyzed electrooxidative [4+2] annulation of primary benzylic alcohols with internal alkynes is described, which enables benzylic alcohols as weakly directing group precursors to access isocoumarins via multiple C-H functionalization. The reaction works well with a broad substrate scope, tolerates a wide range of functional groups, and incorporates practically the isocoumarin unit into diverse bioactive molecules. Mechanistic studies indicate that activation of aryl C(sp2)-H bonds is achieved through the generation of the active benzoyloxy-Ru(ii) intermediates via oxidation of benzylic alcohols using an electrooxidative Ru(ii) catalyst.
Luo, Mu-Jia,Hu, Ming,Song, Ren-Jie,He, De-Liang,Li, Jin-Heng
supporting information
p. 1124 - 1127
(2019/01/28)

Effect of Substituents on Partial Photocatalytic Oxidation of Aromatic Alcohols Assisted by Polymeric C3N4
In the present work we scrutinize the effect of substituents in the phenyl ring of the benzyl alcohol on its photo-oxidation to the corresponding benzaldehyde driven by polymeric carbon nitride photocatalyst in aqueous medium. It has been established that electron donating (ED) substituents in para- and ortho-position with respect to the CH2OH-group promote the reactivity of the substrate without compromising the selectivity towards benzaldehyde formation, maintaining it in the range of 84–98 %, if compared to the unsubstituted molecule. The same observation is true for meta-substituted benzyl alcohol with an electron withdrawing (EW) group. On the other hand, the presence of ED-group in meta-position or EW-group in para-position with respect to the CH2OH-group reduces the reactivity as well as the selectivity towards the aldehyde production, resulting in the values of selectivity ranging from 40 to 80 %. Quantum chemical calculations have allowed to establish that the reactivity correlates with the positive charge on the benzylic carbon in benzyl alcohol cation intermediate, while the selectivity, most probably, is conditioned by a negative charge on the carbon atoms in the phenyl ring being a target for an electrophile attack. The modification of the polymeric C3N4 photocatalyst with H2O2 reduces the unselective benzyl alcohol oxidation, thus favouring the higher selectivity towards benzaldehyde production.
Krivtsov, Igor,Ilkaeva, Marina,García-López, Elisa I.,Marcì, Giuseppe,Palmisano, Leonardo,Bartashevich, Ekaterina,Grigoreva, Ekaterina,Matveeva, Ksenia,Díaz, Eva,Ordó?ez, Salvador
p. 2713 - 2724
(2019/05/28)

A transition metal free expedient approach for the C[dbnd]C bond cleavage of arylidene Meldrum's acid and malononitrile derivatives
A transition metal free expedient approach for the C[dbnd]C bond cleavage of electron deficient alkenes such as arylidene Meldrum's acid and malononitrile derivatives are discussed. The C[dbnd]C bond of these compound were cleaved to benzoic acid in good yield at high temperature. Most importantly, with oxone in CH3CN/H2O at 45 °C or m-CPBA in DCM or NaClO2 in THF/H2O or PIDA in THF at room temperature furnished benzaldehyde derivatives selectively in excellent yields.
Suresh, Muthiah,Kumari, Anusueya,Singh, Raj Bahadur
(2019/09/10)

On/Off O2 Switchable Photocatalytic Oxidative and Protodecarboxylation of Carboxylic Acids
Photoredox catalysis in recent years has manifested a powerful branch of science in organic synthesis. Although merging photoredox and metal catalysts has been a widely used method, switchable heterogeneous photoredox catalysis has rarely been considered. Herein, we open a new window to use a switchable heterogeneous photoredox catalyst which could be turned on/off by changing a simple stimulus (O2) for two opponent reactions, namely, oxidative and protodecarboxylation. Using this strategy, we demonstrate that Au@ZnO core-shell nanoparticles could be used as a switchable photocatalyst which has good catalytic activity to absorb visible light due to the localized surface plasmon resonance effect of gold, can decarboxylate a wide range of aromatic and aliphatic carboxylic acids, have multiple reusability, and are a reasonable candidate for synthesizing both aldehydes/ketones and alkane/arenes in a large-scale set up. Some biologically active molecules are also shown via examples of the direct oxidative and protodecarboxylation which widely provided pharmaceutical agents.
Bazyar, Zahra,Hosseini-Sarvari, Mona
p. 13503 - 13515
(2019/10/11)

Assessment of the regioselectivity in the condensation reaction of unsymmetrical o-phthaldialdehydes with alanine
One approach for the synthesis of isoindolinones, a privileged bioactive heterocyclic core structure, involves a condensation reaction of o-phthaldialdehydes with a suitable nitrogen-containing nucleophile. This fascinating reaction is revisited here in the context of the use of o-phthaldialdehydes that contain additional substituents in the aromatic ring leading to a detailed analysis of the regioselectivity of the reaction. Eleven monosubstituted o-phthaldialdehydes were synthesised and reacted with alanine. The regioselectivity observed across the eleven substrates led to the design of a disubstituted substrate that reacted with very high control. A gram-scale reaction followed by esterification gave one major regioisomer in high yield. In addition, the regioselectivity observed on reaction of two novel monodeuterated substrates led to an increased mechanistic understanding.
D'Hollander, Agathe C.A.,Westwood, Nicholas J.
p. 224 - 239
(2017/12/08)

Stereoselective synthesis of 5′-hydroxyzearalenone
A first stereoselective total synthesis of 14-memebered β-resorcylic macrolactone 5′-hydroxyzearalenone (1) has been achieved. The key steps are Jocobsen hydrolytic kinetic resolution, Sharpless asymmetric dihydroxylation, Vilsmeier-Haack reaction, Mitsunobu esterification and ring-closing metathesis.
Avuluri, Srilatha,Bujaranipalli, Sheshurao,Das, Saibal,Yadav
p. 3547 - 3549
(2018/08/29)

CO2-Catalyzed oxidation of benzylic and allylic alcohols with DMSO
CO2-catalyzed transition-metal-free oxidation of alcohols has been achieved. Earlier, several methodologies have been explored for alcohol oxidations based on transition-metal catalysts. However, owing to the cheaper price, easy separation and nontoxicity, transition-metal-free systems are in high demand to the pharmaceutical industries. For this reason, various primary and secondary alcohols have been selectively oxidized to the corresponding carbonyl compounds using CO2 as a catalyst in the presence of different functional groups such as nitrile, nitro, aldehyde, ester, halogen, ether, and so on. At the end, transition-metal-free syntheses of pharmaceuticals have also been achieved. Finally, the role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments and DFT calculations.
Riemer, Daniel,Mandaviya, Bhavdip,Schilling, Waldemar,G?tz, Anne Charlotte,Kühl, Torben,Finger, Markus,Das, Shoubhik
p. 3030 - 3034
(2018/04/14)

Highly Productive Oxidative Biocatalysis in Continuous Flow by Enhancing the Aqueous Equilibrium Solubility of Oxygen
We report a simple, mild, and synthetically clean approach to accelerate the rate of enzymatic oxidation reactions by a factor of up to 100 when compared to conventional batch gas/liquid systems. Biocatalytic decomposition of H2O2 is used to produce a soluble source of O2 directly in reaction media, thereby enabling the concentration of aqueous O2 to be increased beyond equilibrium solubility under safe and practical conditions. To best exploit this method, a novel flow reactor was developed to maximize productivity (g product L?1 h?1). This scalable benchtop method provides a distinct advantage over conventional bio-oxidation in that no pressurized gas or specialist equipment is employed. The method is general across different oxidase enzymes and compatible with a variety of functional groups. These results culminate in record space-time yields for bio-oxidation.
Chapman, Michael R.,Cosgrove, Sebastian C.,Turner, Nicholas J.,Kapur, Nikil,Blacker, A. John
supporting information
p. 10535 - 10539
(2018/08/17)

Method for synthesizing pharmaceutical intermediate 3,5-dimethoxybenzaldehyde
The invention discloses a method for synthesizing pharmaceutical intermediate 3,5-dimethoxybenzaldehyde. The method comprises the steps of adding 2-bromine-3,5-dimethoxybenzyl alcohol and a potassiumnitrate solution to a reaction vessel, controlling stirring speed, increasing the temperature of the solution, adding lead tetraacetate powder and an aqueous solution, and conducting reaction; addinga 3-methylpentane solution and bismuth disulfide powder, raising the temperature, continuing the reaction, reducing the temperature of the solution, adding a sodium sulfate solution, standing, waitingthe situation that the solution is layered, washing with an anisole solution, recrystallizing in a dipropylene glycol solution, and dehydrating to obtain the finished 3,5-dimethoxybenzaldehyde with dehydrating agent.
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Paragraph 0016-0018; 0020-0026

(2018/07/30)

Nickel boride mediated chemoselective deprotection of 1,1-diacetates to aldehydes and deprotection with concomitant reduction to alcohols at ambient temperature
A variety of 1,1-diacetates have been chemoselectively and efficiently deprotected to the corresponding aldehydes as well as deprotected and concomitantly reduced to the corresponding alcohols in high yields at ambient temperature with nickel boride generated in situ using different molar ratios of sodium borohydride and nickel (II) chloride in methanol at room temperature. Deprotection and reduction of a variety of aromatic, aliphatic and heterocyclic acylals have been achieved efficiently. Mild reaction conditions, easy work-up, high yields and chemoselectivity demonstrate the efficiency of this new method.
Bartwal, Gaurav,Saroha, Mohit,Khurana, Jitender.M.
p. 97 - 103
(2017/12/28)

Dehydrogenative Formation of Resorcinol Derivatives Using Pd/C-Ethylene Catalytic System
The conversion of substituted 1,3-cyclohexanediones to the alkyl ethers of resorcinol using a Pd/C-ethylene system is reported. In these reactions, ethylene works as a hydrogen acceptor. The efficient synthesis of resveratrol was achieved using this protocol as a key step. In addition, the direct formation of substituted resorcinols was carried out by adding K2CO3 into the reaction media.
El-Deeb, Ibrahim Yussif,Funakoshi, Tatsuya,Shimomoto, Yuya,Matsubara, Ryosuke,Hayashi, Masahiko
p. 2630 - 2640
(2017/03/14)

Method for synthesizing aryl formaldehyde compound from aryl formate compound
The invention discloses a method for synthesizing an aryl formaldehyde compound from an aryl formate compound. The method comprises the following steps: taking the aryl formate compound as a raw material, and reacting under the action of excessive hydrazine hydrate; after the end of the reaction, standing, cooling, filtering and washing, thus respectively obtaining filtrate and filter cake, wherein the filtrate is the hydrazine hydrate, and the filter cake is an aryl formylhydrazine compound; recycling and reusing the filtrate; then dissolving the aryl formylhydrazine compound in a solvent, reacting under the existence of 2-iodoxybenzoic acid and alkali, and carrying out aftertreatment, thus obtaining the aryl formaldehyde compound and a byproduct-2-iodosobenzoic acid; regenerating the 2-iodoxybenzoic acid after oxidizing the 2-iodosobenzoic acid, and repeatedly using the 2-iodoxybenzoic acid. According to the method disclosed by the invention, recycling and cyclic utilization of materials are fully realized, emissions are less, environment friendliness is realized, and the yield is higher.
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Paragraph 0042-0043

(2017/07/06)

Selective Copper-N-Heterocyclic Carbene (Copper-NHC)-Catalyzed Aerobic Cleavage of β-1 Lignin Models to Aldehydes
As fossil resources are undergoing fast depletion, the harvesting of sustainable aromatic compounds from biorenewable lignin has become highly appealing nowadays. However, the development of efficient catalysts for lignin depolymerization to high value-added chemicals is challenging. In this paper, a selective copper-N-heterocyclic carbene (copper-NHC)-catalyzed aerobic cleavage is reported for β-1 lignin model compound, which represents an important family of natural wood lignin. Using this catalyst system, the cleavage of β-1 model compounds gave >99% conversions and satisfactory yields of the corresponding aldehydes, which can serve as versatile starting materials for the chemical industry.
Zhou, Zhong-Zhen,Liu, Mingxin,Li, Chao-Jun
p. 3344 - 3348
(2017/06/09)

Oxidative decarboxylation of arylacetic acids in water: One-pot transition-metal-free synthesis of aldehydes and ketones
One-pot transition-metal-free synthesis of aromatic aldehydes and ketones via oxidative decarboxylation of arylacetic acids in water is developed. Protocol relies on the direct decarboxylation of sp3-hybridized carbon in water without any over oxidation into carboxylic acids with minimal waste. Reaction mechanism is investigated and application of this protocol is demonstrated on a gram scale.
Mete, Trimbak B.,Khopade, Tushar M.,Bhat, Ramakrishna G.
supporting information
p. 2822 - 2825
(2017/06/27)

Visible light mediated chemo-selective oxidation of benzylic alcohols
A highly chemoselective visible light mediated strategy has been developed for oxidation of benzylic alcohols. The method circumvents the use of toxic metal catalysts, high energy light source, and operates at room temperature. Furthermore reaction is easily scalable to gram levels.
Devari, Shekaraiah,Rizvi, Masood Ahmad,Shah, Bhahwal Ali
supporting information
p. 3294 - 3297
(2016/07/11)

Solid state red biphotonic excited emission from small dipolar fluorophores
Dyes emitting in the solid state in the red or near-infrared range are much sought after for application in bioimaging especially if the long emission wavelength can be combined with two-photon excitation to provide unique contrast and penetration depth. In this article we present a series of small push-pull dipolar fluorophores based on 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofurane as electron accepting group. Compounds 1a-1m differ only by the number (one, two or three) and the position of methoxy groups on the electron-donor part. If these compounds are weakly emissive in dilute solution, they exhibit aggregation-induced emission properties and exciting solid state emission in the red - near infrared range very different from one compound to another highlighting the role of the number and of the position of the methoxy electron-donor groups. The solid-state properties were studied by fluorescence spectroscopy and the solid state structures were analyzed by X-ray diffraction showing the presence of a long chain of specific aggregates for the emitting species. Finally, the two-photon excitation properties were measured over the range 780-920 nm directly on the solid.
Ipuy, Martin,Liao, Yuan-Yuan,Jeanneau, Erwann,Baldeck, Patrice L.,Bretonnière, Yann,Andraud, Chantal
supporting information
p. 766 - 779
(2016/02/03)

Design and synthesis of a series of serine derivatives as small molecule inhibitors of the SARS coronavirus 3CL protease
Synthesis of serine derivatives having the essential functional groups for the inhibitor of SARS 3CL protease and evaluation of their inhibitory activities using SARS 3CL R188I mutant protease are described. The lead compounds, functionalized serine derivatives, were designed based on the tetrapeptide aldehyde and Bai's cinnamoly inhibitor, and additionally performed with simulation on GOLD softwear. Structure activity relationship studies of the candidate compounds were given reasonable inhibitors ent-3 and ent-7k against SARS 3CL R188I mutant protease. These inhibitors showed protease selectivity and no cytotoxicity.
Konno, Hiroyuki,Wakabayashi, Masaki,Takanuma, Daiki,Saito, Yota,Akaji, Kenichi
supporting information
p. 1241 - 1254
(2016/03/01)

SKIN LIGHTENING COMPOUNDS
The present invention provides a compound of Formula I, II or III or a salt or prodrug derivative thereof that is a skin-lightening agent useful for the inhibition of melanin synthesis and/or the removal of existing melanin to function as a skin-lightening agent.
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Page/Page column 25

(2016/02/12)

A straightforward and versatile protocol for the direct conversion of benzylic azides to ketones and aldehydes
The synthesis of carbonyl compounds from benzylic azides through benzylideneamides is described for the first time. NaH-mediated activation of benzyl azides allows a rapid water-promoted oxidation under a facile protocol with good yields.
González-Calderón, Davir,Morales-Reza, Marco A.,Díaz-Torres, Eduardo,Fuentes-Benítes, Aydeé,González-Romero, Carlos
p. 83547 - 83550
(2016/10/12)

Formation and characterization of a reactive chromium(V)-oxo complex: Mechanistic insight into hydrogen-atom transfer reactions
A mononuclear Cr(V)-oxo complex, [CrV(O)(6-COO--tpa)](BF4)2 (1; 6-COO--tpa = N,N-bis(2-pyridylmethyl)-N-(6-carboxylato-2-pyridylmethyl)amine) was prepared through the reaction of a Cr(III) precursor complex with iodosylbenzene as an oxidant. Characterization of 1 was achieved using ESI-MS spectrometry, electron paramagnetic resonance, UV-vis, and resonance Raman spectroscopies. The reduction potential (Ered) of 1 was determined to be 1.23 V vs. SCE in acetonitrile based on analysis of the electron-transfer (ET) equilibrium between 1 and a one-electron donor, [RuII(bpy)3]2+ (bpy = 2,2′-bipyridine). The reorganization energy (λ) of 1 was also determined to be 1.03 eV in ET reactions from phenol derivatives to 1 on the basis of the Marcus theory of ET. The smaller λ value in comparison with that of an Fe(IV)-oxo complex (2.37 eV) is caused by the small structural change during ET due to the dπ character of the electron-accepting LUMO of 1. When benzyl alcohol derivatives (R-BA) with different oxidation potentials were employed as substrates, corresponding aldehydes were obtained as the 2e--oxidized products in moderate yields as determined from 1H NMR and GC-MS measurements. One-step UV-vis spectral changes were observed in the course of the oxidation reactions of BA derivatives by 1 and a kinetic isotope effect (KIE) was observed in the oxidation reactions for deuterated BA derivatives at the benzylic position as substrates. These results indicate that the rate-limiting step is a concerted proton-coupled electron transfer (PCET) from substrate to 1. In sharp contrast, in the oxidation of trimethoxy-BA (Eox = 1.22 V) by 1, trimethoxy-BA radical cation was observed by UV-vis spectroscopy. Thus, it was revealed that the mechanism of the oxidation reaction changed from one-step PCET to stepwise ET-proton transfer (ET/PT), depending on the redox potentials of R-BA.
Kotani, Hiroaki,Kaida, Suzue,Ishizuka, Tomoya,Sakaguchi, Miyuki,Ogura, Takashi,Shiota, Yoshihito,Yoshizawa, Kazunari,Kojima, Takahiko
p. 945 - 955
(2015/02/05)

Mechanistic studies of copper(I)-catalyzed 1,3-halogen migration
An ongoing challenge in modern catalysis is to identify and understand new modes of reactivity promoted by earth-abundant and inexpensive first-row transition metals. Herein, we report a mechanistic study of an unusual copper(I)-catalyzed 1,3-migration of 2-bromostyrenes that reincorporates the bromine activating group into the final product with concomitant borylation of the aryl halide bond. A combination of experimental and computational studies indicated this reaction does not involve any oxidation state changes at copper; rather, migration occurs through a series of formal sigmatropic shifts. Insight provided from these studies will be used to expand the utility of aryl copper species in synthesis and develop new ligands for enantioselective copper-catalyzed halogenation.
Van Hoveln, Ryan,Hudson, Brandi M.,Wedler, Henry B.,Bates, Desiree M.,Le Gros, Gabriel,Tantillo, Dean J.,Schomaker, Jennifer M.
supporting information
p. 5346 - 5354
(2015/05/13)

Photodegradation of methoxy substituted curcuminoids
Photodegradation of dimethoxy curcuminoids in acetonitrile solution was found to depend on the position of the methoxy group bonded to the phenyl ring. The rate of decomposition was expressed as the lifetime of the decomposing substrate, being the shortest in the case of the 3,5-dimethoxy and the longest for the 2,5-dimethoxy derivative. For the 3,5-dimethoxy curcuminoid, the major degradation products were 3,5-dimethoxybenzaldehyde, 3,5-dimethoxybenzoic acid and the Z and E isomers of dimethoxycinnamic acid, together forming about 90% of the reaction mixture. Minor products found were 4,5-bis(3,5-dimethoxyphenyl)hex-2-endionic acid, products with the molecular formula C23H24O6 and C23H22O6 attributed to the reaction of intramolecular [2 + 2] cycloaddition of the dimethoxy curcuminoid, and the dioxygenated bicyclopentadione derivative (C23H24O8) derived from autoxidative transformation of the dimethoxy curcuminoid.
Galer, Petra,?ket, Boris
p. 346 - 353
(2015/06/30)

Palladium-catalyzed carbonylations of aryl bromides using paraformaldehyde: Synthesis of aldehydes and esters
Carbonylation reactions represent useful tools for organic synthesis. However, the necessity to use gaseous carbon monoxide is a disadvantage for most organic chemists. To solve this problem, novel protocols have been developed for conducting palladium-catalyzed reductive carbonylations of aryl bromides and alkoxycarbonylations using paraformaldehyde as an external CO source (CO gas free). Hence, aromatic aldehydes and esters were synthesized in moderate to good yields.
Natte, Kishore,Dumrath, Andreas,Neumann, Helfried,Beller, Matthias
supporting information
p. 10090 - 10094
(2015/03/31)

Synthesis and biological evaluation of Hydrazone derivatives as antifungal agents
Emerging yeasts are among the most prevalent causes of systemic infections with high mortality rates and there is an urgent need to develop specific, effective and non-Toxic antifungal agents to respond to this issue. In this study 35 aldehydes, hydrazones and hydrazines were obtained and their antifungal activity was evaluated against Candida species (C. parapsilosis, C.Tropicalis, C. krusei, C. albicans, C. glabrata and C. lusitaneae) and Trichosporon asahii, in an in vitro screening. The minimum inhibitory concentrations (MICs) of the active compounds in the screening was determined against 10 clinical isolates of C. parapsilosis and 10 of T. asahii. The compounds 4-pyridin-2-ylbenzaldehyde] (13a) and tert-butyl-(2Z)-2-(3,4,5-Trihydroxybenzylidine)hydrazine carboxylate (7b) showed the most promising MIC values in the range of 16-32 μg/mL and 8-16 μg/mL, respectively. The compounds' action on the stability of the cell membrane and cell wall was evaluated, which suggested the action of the compounds on the fungal cell membrane. Cell viability of leukocytes and an alkaline comet assay were performed to evaluate the cytotoxicity. Compound 13a was not cytotoxic at the active concentrations. These results support the discovery of promising candidates for the development of new antifungal agents.
Casanova, Bruna B.,Muniz, Mauro N.,De Oliveira, Thayse,De Oliveira, Luís Flavio,Machado, Michel M.,Fuentefria, Alexandre M.,Gosmann, Grace,Gnoatto, Simone C. B.
p. 9229 - 9241
(2016/08/31)

Magnetic copper ferrite nanoparticles/TEMPO catalyzed selective oxidation of activated alcohols to aldehydes under ligand- and base-free conditions in water
A novel, effective and sustainable strategy for the synthesis of aldehydes has been developed using inexpensive, readily available, oxygen-stable and recyclable CuFe2O4 nanoparticles as the catalyst. The corresponding substituted aldehydes were obtained in moderate to good yields by aerobic oxidation of aromatic alcohols in water under dioxygen atmosphere. Importantly, a ligand or a base was not necessary. The catalyst was completely recoverable with an external magnet and could be reused six times without significant loss of catalytic activity.
Zhu, Xiao,Yang, Daoshan,Wei, Wei,Jiang, Min,Li, Lulu,Zhu, Xiangbing,You, Jinmao,Wang, Hua
p. 64930 - 64935
(2015/04/27)

Aerobic oxidation of alcohols by using a completely metal-free catalytic system
A metal-free reaction system of air, NH4NO3(cat), 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)(cat), and H +(cat) is introduced as a simple, safe, inexpensive, efficient and chemoselective mediator for aerobic oxidation of various primary and secondary benzyl and alkyl alcohols, including those bearing oxidizable heteroatoms (N, S, O) to the corresponding aldehydes or ketones. Air oxygen under slight overpressure plays the role of the terminal oxidant, which is catalytically activated by redox cycles of nitrogen oxides released from a catalytic amount of NH4NO3 and cocatalyzed by TEMPO (nitroxyl radical compound), under acidic conditions, which are essential for an overall activation of the reaction system. The synthetic value of this reaction system and its green chemical profile was illustrated by a 10 g scale-up experiment, performed in an open-air system by using a renewable and reusable polymer-supported form of TEMPO (OXYNITROXS100). The reaction solvent was recovered by distillation under atmospheric pressure, and the pure final product was isolated under reduced pressure; the acid activators (HCl or H 2SO4) were recovered as ammonium salts. A metal-free reaction system of air/NH4NO3(cat)/TEMPO (cat)/H+(cat) is introduced as a simple, safe, inexpensive, efficient and chemoselective mediator for aerobic oxidation of various primary and secondary benzyl, alkyl and allyl alcohols, including those bearing oxidizable heteroatoms (N, S, O) to the corresponding aldehydes or ketones. Copyright
Prebil, Rok,Stavber, Gaj,Stavber, Stojan
supporting information
p. 395 - 402
(2014/01/23)

Aerobic Oxidation of Alcohols by Using a Completely Metal-Free Catalytic System
A metal-free reaction system of air, NH4NO3(cat), 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)(cat), and H+(cat) is introduced as a simple, safe, inexpensive, efficient and chemoselective mediator for aerobic oxidation of various primary and secondary benzyl and alkyl alcohols, including those bearing oxidizable heteroatoms (N, S, O) to the corresponding aldehydes or ketones. Air oxygen under slight overpressure plays the role of the terminal oxidant, which is catalytically activated by redox cycles of nitrogen oxides released from a catalytic amount of NH4NO3 and cocatalyzed by TEMPO (nitroxyl radical compound), under acidic conditions, which are essential for an overall activation of the reaction system. The synthetic value of this reaction system and its green chemical profile was illustrated by a 10 g scale-up experiment, performed in an open-air system by using a renewable and reusable polymer-supported form of TEMPO (OXYNITROXS100). The reaction solvent was recovered by distillation under atmospheric pressure, and the pure final product was isolated under reduced pressure; the acid activators (HCl or H2SO4) were recovered as ammonium salts.
Prebil, Rok,Stavber, Gaj,Stavber, Stojan
supporting information
p. 395 - 402
(2015/10/05)

TEMPO-mediated oxidation of primary alcohols to aldehydes under visible light and air
A homogeneous visible light photoredox TEMPO-mediated selective oxidation of primary alcohols to the corresponding carbonyl compounds was developed using molecular oxygen from air as the terminal oxidant. Ru(bpy)3(PF 6)2 (bpy: bipyridyl) and Ir(dtb-bpy)(ppy) 2(PF6) (dtb-bpy: 4,4′-di-tert-butyl-2,2′- bipyridyl; ppy: 2-phenylpyridine) were used as the sensitizers. A homogeneous visible light photoredox TEMPO-mediated selective oxidation of primary alcohols to the corresponding carbonyl compounds was developed. Molecular oxygen from air was the terminal oxidant. Copyright
Liu, Dongwang,Zhou, Hongxia,Gu, Xiangyong,Shen, Xiaoqin,Li, Pixu
supporting information
p. 117 - 122
(2014/03/21)

Copper catalysts for selective c-c bond cleavage of b-o-4 lignin model compounds
The reactivity of homogeneous copper catalysts towards the selective C-C bond cleavage of both phenolic and non-phenolic arylglycerol b-aryl ether lignin model compounds has been explored. Several copper precursors, nitrogen ligands, and solvents were evaluated in order to optimize the catalyst system. Using the optimized catalyst system, copper(I) trifluoromethanesulfonate [CuACHTUNGTRENUNG(OTf)]/L/TEMPO (L=2,6-lutidine, TEMPO=2,2,6,6-tetramethyl-piperidin-1-yl-oxyl), aerobic oxidation of the non-phenolic b-O-4 lignin model compound proceeded with good selectivity for Ca-Cb bond cleavage, affording 3,5-dimethoxybenzaldehyde as the major product. Aerobic oxidation of the corresponding phenolic b-O-4 lignin model proceeded with different selectivity, affording 2,6-dimethoxybenzoquinone and a,b-unsaturated aldehyde products resulting from cleavage of the CaCaryl bond. At low catalyst concentrations, however, a change in selectivity was observed as oxidation of the benzylic secondary alcohol predominated with both substrates.
Sedai, Baburam,Tom Baker
supporting information
p. 3563 - 3574
(2015/01/09)

Copper catalysts for selective C-C bond cleavage of β-O-4 lignin model compounds
The reactivity of homogeneous copper catalysts towards the selective C-C bond cleavage of both phenolic and non-phenolic arylglycerol β-aryl ether lignin model compounds has been explored. Several copper precursors, nitrogen ligands, and solvents were evaluated in order to optimize the catalyst system. Using the optimized catalyst system, copper(I) trifluoromethanesulfonate [CuACHTUNGTRENUNG(OTf)]/L/ TEMPO (L=2,6-lutidine, TEMPO=2,2,6,6-tetramethyl- piperidin-1-yl-oxyl), aerobic oxidation of the non-phenolic β-O-4 lignin model compound proceeded with good selectivity for Cα-Cβ bond cleavage, affording 3,5-dimethoxybenzaldehyde as the major product. Aerobic oxidation of the corresponding phenolic β-O-4 lignin model proceeded with different selectivity, affording 2,6-dimethoxybenzoquinone and a,β-unsaturated aldehyde products resulting from cleavage of the Ca-Caryl bond. At low catalyst concentrations, however, a change in selectivity was observed as oxidation of the benzylic secondary alcohol predominated with both substrates.
Sedai, Baburam,Baker, R. Tom
p. 3563 - 3574
(2015/02/19)

Selective deoxygenation of hydroxybenzaldehydes
A method for selective deoxygenation of hydroxybenzaldehydes including, condensing syringaldehyde (3,5-dimethoxy-4-hydroxybenzaldehyde) and a functionalized phenylacetic acid with at least one first base and at least one anhydride to produce an arylcinnamic acid, decarboxylating of said arylcinnamic acid with at least one decarboxylation catalyst at temperatures ranging from about 30° C. to 200° C. or thermally at temperatures ranging from about 100° C. to 350° C. to produce a first stilbene, hydrodeoxygenating the stilbene by conversion to a sulfonate in the presence of at least one second base in water or at least one organic solvent to yield a sulfonate reducing the sulfonate(s) with a reductive elimination catalyst to produce a second stilbene, and reacting the second stilbene with a hydrolyzing agent to generate a polyphenol.
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(2015/01/07)

Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes: A protecting-group economic synthesis of phenolic stilbenes
4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4′-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior. The Royal Society of Chemistry 2013.
Schmidt, Bernd,Elizarov, Nelli,Berger, René,H?lter, Frank
supporting information
p. 3674 - 3691
(2013/06/27)

A scalable process for the synthesis of (E)-pterostilbene involving aqueous Wittig olefination chemistry
A synthetic approach toward the pharmacologically active (E)-stilbene pterostilbene is described using a Wittig reaction conducted under mildly basic, aqueous conditions. A surprising, non-intuitive difference in (E)/(Z) stereoselectivity was observed comparing the two possible isomeric Wittig routes, allowing for the development of a highly efficient process to access the title stilbene derivative through a one-pot olefination deprotection sequence.
McNulty, James,McLeod, David
supporting information
p. 6303 - 6306
(2013/11/06)

Aerobic oxidation of β-1 lignin model compounds with copper and oxovanadium catalysts
The reactivity of homogeneous oxovanadium and copper catalysts toward aerobic oxidation of phenolic and nonphenolic β-1 lignin model compounds has been investigated. Aerobic oxidation of diastereomeric, nonphenolic β-1 lignin models (1T, 1E) using the six-coordinate vanadium complex (HQ) 2VV(O)(OiPr) (HQ = 8-oxyquinolinate) as a precatalyst in pyridine afforded ketone (3) and dehydrated ketone (4) derived from oxidation of the secondary alcohol. In contrast, using CuOTf/2,6-lutidine/ TEMPO (OTf = trifluoromethanesulfonate, TEMPO = 2,2,6,6-tetramethyl-piperidin-1- yl-oxyl) in toluene for the same reaction afforded 3,5-dimethoxybenzaldehyde (5) and 4-methoxybenzaldehyde (6) as major products resulting from C α-Cβ bond cleavage. Reactions of the corresponding phenolic lignin model compounds (2T, 2E) with 10 mol % CuOTf/2,6-lutidine/TEMPO gave ketone (9) as the major product, whereas 10 mol % (HQ)2VV(O)(OiPr) or a stoichiometric amount of CuOTf/2,6-lutidine/TEMPO yielded 2,6-dimethoxybenzoquinone (10) as the major product, arising from cleavage of the Caryl-Cα bond. Different selectivity was observed in the oxidation of 2T, 2E using the five-coordinate complex (dipic)VV(O)(OiPr) (dipic = dipicolinate), with α,β-unsaturated aldehyde (14) as the major product (formed from oxidation of the primary alcohol and dehydration). The key differences in chemoselectivity between the vanadium and copper catalysts in the oxidations of these phenolic and nonphenolic β-1 lignin models are discussed.
Sedai, Baburam,Diaz-Urrutia, Christian,Baker, R. Tom,Wu, Ruilian,Silks, L. A. Pete,Hanson, Susan K.
p. 3111 - 3122
(2014/01/06)