Article
Chemistry, Organic
Laxman Devidas Khalse, Prasanta Ghorai
Summary: An efficient cascade protocol for the stereoselective synthesis of borylated carbocycles has been developed. This approach involves copper-catalyzed borylative Michael/Michael cyclization and allows the preparation of 24 new boronic ester substituted indanes, cyclohexanes, and cyclopentanes in good yields with excellent diastereoselectivities and functional group tolerance. The synthetic transformation of carbacyclic boronates was also successfully demonstrated, and gram-scale synthesis was carried out effectively.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hu Tian, Hong-Ming Zhang, Liang Yin
Summary: In this article, a copper(I)-catalyzed asymmetric conjugate addition/protonation with selenols and alpha-substituted alpha,beta-unsaturated thioamides is described, which produces a series of chiral selenides with high to excellent enantioselectivity. The reaction shows a broad substrate scope for both selenols and alpha-substituted alpha,beta-unsaturated thioamides. The catalytic system is also successfully used for asymmetric selenation of beta-substituted alpha,beta-unsaturated thioamides. A [Cu-(R,R-P)-TANIAPHOS]-SePh species is identified by Se-77 NMR spectra, with a chemical shift at delta 462 ppm. Furthermore, a {[Cu-(R)-TOL-BINAP]-SePh}(2) species is characterized by X-ray analysis, confirming the formation of Cu-Se bond in the reaction. Finally, the straightforward transformations of the thioamide group to amine and thioester are demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Soshi Nishino, Yuji Nishii, Koji Hirano
Summary: A copper-catalyzed reaction has been developed for the regio- and diastereoselective borylamination of alpha,beta-unsaturated esters with B(2)pin(2) and hydroxylamines. The reaction delivers acyclic beta-boryl-alpha-amino acid derivatives with high anti-diastereoselectivity, which is difficult to achieve using established methods. Furthermore, the use of a chiral phosphoramidite ligand allows for the enantioselective synthesis of optically active beta-borylated alpha-amino acids. The resulting products can be further transformed into beta-functionalized alpha-amino acids, which are of great interest in medicinal chemistry.
Article
Chemistry, Organic
Laxman Devidas Khalse, Sachin S. Gorad, Prasanta Ghorai
Summary: In this study, a new Cu(II)-(S,S)-Pr-i-FOXAP catalyst was reported for the borylative Michael/Michael addition cascade cyclization of unsymmetrical dienone, leading to the synthesis of highly substituted and functionalized spiroindane boronates under mild conditions. A series of optically active spiroids bearing boronic ester were obtained with excellent yields and good to excellent enantioselectivities and diastereoselectivities.
Article
Chemistry, Organic
Meng Li, Guang-Rui Peng, Xuan Yang, Zhen-Ning Ma, Jian-Bo Xie
Summary: We developed a copper-catalyzed enantio- and diastereoselective boron conjugate addition method for α-alkyl α,beta-unsaturated esters under base-free conditions. The approach exhibited excellent enantioselectivities and moderate to good conversions, although with moderate diastereoselectivities. The synthetic utility of this protocol was demonstrated.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Applied
Brigita Mudrakova, Peter Kisszekelyi, Denisa Vargova, Dorota Zakiewicz, Radovan Sebesta
Summary: This paper presents a highly enantio- and diastereoselective tandem transformation method, using Cu-catalyzed conjugate addition of Grignard reagents to heterocyclic Michael acceptors, followed by one-pot trapping of in situ formed enolates with stabilized carbocations or their equivalents. This method allows the installation of structurally attractive substituents on heterocyclic compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Daniel Rozsar, Alistair J. M. Farley, Iain McLauchlan, Benjamin D. A. Shennan, Ken Yamazaki, Darren J. Dixon
Summary: This article describes the enantioselective intermolecular conjugate addition of nitroalkanes to unactivated alpha,beta-unsaturated esters catalyzed by a bifunctional iminophosphorane (BIMP) superbase. It provides a straightforward approach to the synthesis of pharmaceutically relevant enantioenriched gamma-nitroesters with unprecedented selectivity. The methodology demonstrates broad substrate scope and has been successfully applied on a gram scale with reduced catalyst loading, allowing for catalyst recovery.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Lanfeng Wei, Wenbo Bai, Zhiyan Hu, Zhiyong Yang, Liang Xu
Summary: The study developed a unified metal-free photooxidative platform for the cleavage of C-heteroatom bonds, using AQDAB complex as the photocatalyst to induce the oxidation process. This method allows for chemoselective cleavage of C-N, C-S, and C-Se bonds, broadening the potential applications of oxidation in synthetic chemistry. It established a photooxidation system for formal carbonylation of C-heteroatom (N, S, Se) bonds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Ndidi U. N. Iwumene, Daniel F. Moseley, Robert D. C. Pullin, Michael C. Willis
Summary: Rhodium-catalyzed hydroacylation reactions can be used to synthesize linear α,β-unsaturated enone intermediates, which can be used to construct diverse substituted saturated O-, N-, and S-heterocycles in a one-pot process. The reaction conditions can be adjusted to selectively form O-heterocycles with high levels of diastereoselectivity.
Article
Chemistry, Multidisciplinary
Shoji Matsumoto, Hayato Marumoto, Motohiro Akazome, Yasuhiko Otani, Tatsuo Kaiho
Summary: The selective reduction of alpha, beta-unsaturated carbonyl compounds to saturated carbonyl compounds was achieved using aqueous HI solution, with the introduction of an aryl group at the alpha or beta position improving yield. The reaction was applicable to compounds containing carboxylic acids and halogen atoms, and the mechanism involved Michael-type addition of iodide followed by reduction of the C-I bond through anionic and radical pathways.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2021)
Article
Chemistry, Organic
Kieran Nicholson, Thomas Langer, Stephen P. Thomas
Summary: The use of stoichiometric organoborane reductants in organic synthesis has been well established. In this study, these reagents were rendered catalytic through an isodesmic B-O/B-H transborylation, enabling borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The proposed mechanism of catalysis involves 1,4-hydroboration and B-O/B-H transborylation as key steps, supported by single-turnover and isotopic labeling experiments.
Article
Chemistry, Physical
Peilin Han, Huijuan Han, Xiaowei Zhang, Xiaoxiao Hou, Hui Wang, Chunhui Liu
Summary: The competing mechanisms of silver-/aminolithium-catalyzed hydrofunctionalization of alpha,beta-unsaturated ester with an amino alcohol were systematically studied using DFT methods. It was found that the OH group in an amino alcohol is easier to deprotonate compared to the NH2 group, and the generated Ag-O bond is more stable than the Ag-N bond, leading to higher reactivity of the OH group in the presence of a Lewis acid/Bronsted base pair catalyst.
THEORETICAL CHEMISTRY ACCOUNTS
(2021)
Article
Chemistry, Multidisciplinary
Sudakar Padmanaban, Yunho Lee, Sungho Yoon
Summary: In this study, a Ru-immobilized bisphosphine-based porous organic polymer (Ru@PP-POP) was used as an efficient heterogeneous catalyst for the chemoselective hydrogenation of cinnamaldehyde to cinnamyl alcohol with high chemoselectivity (98%) and excellent recyclability. The catalyst showed a high turnover number (970) and a high turnover frequency (240h^-1), representing the best activity obtained using a phosphine-based heterogeneous Ru-catalyst in this transformation.
JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Changli He, Xiaoxue Tang, Xin He, Yuqiao Zhou, Xiaohua Liu, Xiaoming Feng
Summary: Reversal of regioselectivity in the catalytic asymmetric conjugate additions of 3-substituted oxindoles to beta-nitroenones or beta-nitroacrylates was achieved with chiral scandium catalysts. Functionalized 3,3-disubstituted oxindoles, including terminal and internal vinyl groups, were constructed in excellent yields and ee values.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Liang Tang, Yicong Luo, Cheng Sheng, Fang Xie, Wanbin Zhang
Summary: This article reports the efficient kinetic resolution of gamma-substituted alpha,beta-unsaturated gamma-lactams via a Cu-catalyzed asymmetric boron conjugate addition, which leads to the synthesis of chiral beta-hydroxy-gamma-lactams with beta,gamma-stereogenic carbon centers. The method is successful with a wide range of substrates and exhibits versatile transformations and synthetic utility in biologically active molecules. Mechanistic studies indicate that a Lewis acid Cu-I-catalyzed mechanism is the likely pathway in the catalytic reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Wen Chen, Lu Sun, Xi Huang, Jiayi Wang, Yanqing Peng, Gonghua Song
ADVANCED SYNTHESIS & CATALYSIS
(2015)
Article
Chemistry, Organic
Jiayi Wang, Qiaoying Shen, Jiayu Zhang, Gonghua Song
TETRAHEDRON LETTERS
(2015)
Article
Chemistry, Organic
Jiayi Wang, Qiaoying Shen, Jiayu Zhang, Gonghua Song
TETRAHEDRON LETTERS
(2015)
Article
Chemistry, Organic
Qing Lu, Qiaoying Shen, Lu Sun, Jiayi Wang, Gonghua Song
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Multidisciplinary
Xi Huang, Mingming Wang, Mengying Wu, Jiayi Wang, Yanqing Peng, Gonghua Song
Article
Chemistry, Organic
Lu Sun, Mengying Wu, Xi Huang, Jiayi Wang, Gonghua Song
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2018)
Article
Chemistry, Multidisciplinary
Jia-Yu Zhang, Xi Huang, Qiao-Ying Shen, Jia-Yi Wang, Gong-Hua Song
CHINESE CHEMICAL LETTERS
(2018)
Article
Chemistry, Multidisciplinary
Haiyang Sun, Hui Li, Jiayi Wang, Gonghua Song
CHINESE CHEMICAL LETTERS
(2018)
Article
Chemistry, Multidisciplinary
Jiayi Wang, Yuan Li, Yanqing Peng, Gonghua Song
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2014)
Article
Biochemistry & Molecular Biology
Yan Shen, Jia-Yi Wang, Gong-Hua Song
MOLECULAR DIVERSITY
(2014)
Article
Biochemistry & Molecular Biology
Jiayi Wang, Beiling Xu, Shanyu Si, Hui Li, Gonghua Song
MOLECULAR DIVERSITY
(2014)
Article
Chemistry, Organic
Yiting Zheng, Lu Sun, Jiayi Wang, Gonghua Song
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2019)
Article
Chemistry, Multidisciplinary
Xi Huang, Juan Li, Xiang Li, Jiayi Wang, Yanqing Peng, Gonghua Song
Article
Engineering, Chemical
Shengjie Lin, Yanqing Peng, Junjie Hu, Jiayi Wang, Yu Li, Gonghua Song
CHEMICAL ENGINEERING & TECHNOLOGY
(2017)
Article
Chemistry, Multidisciplinary
Xuemei Liu, Chaonan Cui, Shuoshuo Wei, Jinyu Han, Xinli Zhu, Qingfeng Ge, Hua Wang
Summary: This study presents a new strategy for designing efficient photocatalysts that can convert CO2 into hydrocarbons by utilizing synergistic catalytic sites. The findings provide a solution for the selective photocatalytic reduction of CO2 to CH4.
Article
Chemistry, Multidisciplinary
Chengxian Hu, Dan Wang, Lu Wang, Ying Fu, Zhengyin Du
Summary: A novel one-pot, three-component reaction conducted under electrochemical conditions was studied. The reaction involved 2-aminothiophenols, aldehydes, and malononitrile, using TBABF4 as an electrolyte and CuI as a catalyst. The proposed reaction mechanism suggested that CuI served as an electron relay. This method offers simplified operation, high atom economy, and mild reaction conditions.
Article
Chemistry, Multidisciplinary
Zhi Yang, Yu Chen, Linxi Wan, Yuxiao Li, Dan Chen, Jianlin Tao, Pei Tang, Fen-Er Chen
Summary: A highly enantioselective method for the complete hydrogenation of pyrimidinium salts using Ir/(S,S)-f-Binaphane complex as the catalyst was developed. This method provides easy access to fully saturated chiral hexahydropyrimidines, which are prevalent in many bioactive molecules. The reactions exhibit high yields and enantioselectivities under mild reaction conditions without additives. Successful application of this methodology in a continuous flow fashion further extends its practical utility.
Article
Chemistry, Multidisciplinary
Tina Jeoh, Jennifer Danger Nill, Wujun Zhao, Sankar Raju Narayanasamy, Liang Chen, Hoi-Ying N. Holman
Summary: In this study, the enzymatic hydrolysis of cellulose was investigated using real-time infrared spectromicroscopy. The spatial heterogeneity of cellulose was found to impact the hydrolysis kinetics. Hydration affected cellulose ordering, and Cel7A preferentially removed less extensively hydrogen bonded cellulose.
Article
Chemistry, Multidisciplinary
Tiphaine Richard, Walid Abdallah, Xavier Trivelli, Mathieu Sauthier, Clement Dumont
Summary: An effective method of grafting functionalities onto lignin based on glycerol carbonate has been developed using an efficient nickel-catalysed telomerisation reaction. This method allows lignin to have new reactive functions and reduces the glass transition temperatures of modified lignins, thereby expanding the application range of lignin-based resins.
Article
Chemistry, Multidisciplinary
Jing Qi, Xiyan Wang, Gan Wang, Srinivas Reddy Dubbaka, Patrick ONeill, Hwee Ting Ang, Jie Wu
Summary: This study presents a green and environmentally friendly approach for the synthesis of imides using electrocatalytic oxidation with H2O as the oxygen source. The method eliminates the need for toxic or expensive oxidants and achieves high yields under mild reaction conditions. It shows broad substrate compatibility and potential for industrial applications.
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang
Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.
Article
Chemistry, Multidisciplinary
Juho Antti Sirvio, Idamaria Romakkaniemi, Juha Ahola, Svitlana Filonenko, Juha P. Heiskanen, Ari Ammala
Summary: This article discusses the method of using supramolecular interaction between an aromatic hydrogen bond donor and lignin to achieve rapid delignification of softwood at low temperatures.
Article
Chemistry, Multidisciplinary
Yunyan Meng, Chunxiang Pan, Na Liu, Hongjiang Li, Zixiu Liu, Yao Deng, Zixiang Wei, Jianbin Xu, Baomin Fan
Summary: A novel visible light-driven synthesis method for 2,3-diamines has been developed, which has mild conditions, avoids the use of metal reagents, and can synthesize diamines and diols in one pot.
Article
Chemistry, Multidisciplinary
Mingqing Huang, Haiyang Huang, Mengyao You, Xinxin Zhang, Longgen Sun, Chao Chen, Zhichao Mei, Ruchun Yang, Qiang Xiao
Summary: A direct air-oxidized strategy for the synthesis of benzo[b]phosphole oxides was developed in this study. Arylphosphine oxides were transformed into phosphinoyl radicals, which were further combined with various alkynes to achieve the desired products. DFT calculations revealed the mechanism of phosphinoyl radical formation.
Article
Chemistry, Multidisciplinary
Anwei Wang, Jiayin Huang, Chunsheng Zhao, Yu Fan, Junfeng Qian, Qun Chen, Mingyang He, Weiyou Zhou
Summary: This study demonstrates an innovative strategy for the aerobic oxidation of C(sp(3))-H bonds using gamma-valerolactone. By optimizing the reaction conditions and utilizing specific catalysts, efficient oxidation of C(sp(3))-H bonds is achieved with good chemoselectivity in certain cases.
Article
Chemistry, Multidisciplinary
Shun Li, Likai Tong, Zhijian Peng, Bo Zhang, Xiuli Fu
Summary: Sulfide compounds show promise as electrocatalysts for water splitting, but their performance is limited by factors such as limited active sites and hindered substance transport. This study successfully prepared a high-entropy sulfide (ZnCoMnFeAlMg)(9)S-8, which reduced grain size and increased specific surface area, enabling the realization of a dual-functional catalyst with multiple catalytic sites. High entropy also modulated the electronic properties of sulfides, reducing the potential energy barrier for hydrolysis. This research introduces a new approach for functionalizing high entropy nanomaterials and improves the performance of water splitting catalysts.