Article
Chemistry, Multidisciplinary
Wei Zhao, Wenji Wang, Huan Zhou, Qishan Liu, Zhiqing Ma, Haizhou Huang, Mingxin Chang
Summary: A one-pot asymmetric hydrogenation of pyridines with subsequent N-alkylation using a traceless Bronsted acid activation strategy is reported. The reaction exhibits high stereoselectivity and can be used to synthesize indolizidines and quinolizidines. Experimental and theoretical studies reveal that chloride anion and noncovalent interactions play important roles in determining the stereoselectivity of the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Zhaofeng Gao, Jingwen Liu, Haizhou Huang, Huiling Geng, Mingxin Chang
Summary: The research reports on efforts to merge two asymmetric reductive amination reactions into a single-step transformation, utilizing specific catalyst and acid additives to successfully synthesize enantiopure secondary amine products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Frank Hollmann, Diederik J. Opperman, Caroline E. Paul
Summary: This review highlights the synthetic state-of-the-art and potential of enzymes catalyzing reductions, ranging from carbonyl, enone, and aromatic reductions to reductive aminations. Enzymes play a key role in producing chiral products with new functionalities, leading to alternative synthetic routes for high-added-value compounds and bulk chemicals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Fengwei Chang, Chengyi Wang, Qipeng Chen, Yongjin Zhang, Guohua Liu
Summary: The combination of biocatalysis and transition-metal catalysis can bridge synthetic gaps in chemical or biological processes, but the deactivation between enzymatic and chemical species poses a significant challenge. Researchers developed an encapsulated Au/carbene and free amine dehydrogenase co-catalyst system, enabling efficient hydration/amination enantioselective cascade reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Zefei Xu, Jinhui Feng, Peiyuan Yao, Qiaqing Wu, Dunming Zhu
Summary: A general chemo-enzymatic approach for the efficient asymmetric synthesis of chiral 3-substituted tetrahydroquinolines has been developed, combining biocatalysis and the Buchwald-Hartwig cross-coupling reaction. The method involves a one-pot ene reductase (ERED)/imine reductase (IRED) cascade and successfully addresses the issue of racemization of the intermediate. This method offers a practical strategy for the construction of chiral 3-substituted tetrahydroquinolines.
Article
Chemistry, Multidisciplinary
Ruke Wang, Xuan Tang, Xinchun Jv, Yaxu Liu, Bo Wang
Summary: In this study, a novel palladium-based nanocatalyst is introduced, which selectively catalyzes the reductive amination of carbonyl compounds, enabling the in situ regeneration of amino donors from wasteful co-products in a one-enzyme cascade using ?-transaminase, without the requirement of the expensive coenzyme NAD(P)H. The cascade combines ?-transaminase-assisted transamination with a selective reductive amination reaction facilitated by a heterogeneous palladium-based nanocatalyst, achieving exceptional yields of chiral amines up to 99% and excellent enantioselectivity. This chemoenzymatic one-enzyme transamination-reductive amination cascade network is highly atom-efficient and generates H2O as its sole by-product, demonstrating its potential impact in synthetic chemistry and beyond.
Article
Chemistry, Multidisciplinary
Qiao Song, Yan Liu, Linlin Cai, Xinyu Cao, Shan Qian, Zhouyu Wang
Summary: This study presents a straightforward method for the synthesis of fused indolizidines and quinolizidines from amides, which is conducted under mild conditions, exhibits good tolerance towards functional groups, can be easily scaled up, and is applicable for the total synthesis of various bioactive substances.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Inorganic & Nuclear
Babulal Maji, Anirban Bhandari, Rayantan Sadhukhan, Joyanta Choudhury
Summary: In this study, water-soluble Ru-NHC complexes were synthesized and tested for their catalytic activity in the transfer hydrogenation of quinoline-type N-heteroarenes using a formic acid/sodium formate buffer solution. The designed ligand within the catalyst backbone exhibited excellent durability, reusability, and compatibility with aqueous-phase operation. The catalytic system demonstrated high efficiency with as little as 0.25 mol% catalyst, providing an overall turnover number of approximately 900.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Physical
Ewald P. J. Jongkind, Aurelie Fossey-Jouenne, Ombeline Mayol, Anne Zaparucha, Carine Vergne-Vaxelaire, Caroline E. Paul
Summary: Accessing chiral amines with high enantiomeric and diastereomeric excess was achieved through the development of a bi-enzymatic cascade using Old Yellow Enzyme family enzymes. Different unsaturated carbonyl substrates were successfully converted with up to 99% selectivity, showcasing the potential of this approach for diverse alkene substrates.
Article
Chemistry, Physical
Kahoko Kato, Dian Deng, Yusuke Kita, Keigo Kamata, Michikazu Hara
Summary: Heterogeneous transition metal catalysts play an important role in the selective synthesis of primary amines. We have discovered a composite material composed of metallic cobalt and silica particles, which exhibits high catalytic performance under mild conditions and addresses the selectivity issues in the production of secondary and tertiary amines. Mechanistic studies revealed that the substrate nitrile and the product amine hinder the hydrogenation of secondary imine intermediates, resulting in a selective reaction. Additionally, the addition of coordinating organic molecules further improves the selectivity for primary amines.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
Article
Chemistry, Organic
Qiao-Fei Bao, Ming Li, Yu Xia, Yu-Zhao Wang, Zhao-Zhao Zhou, Yong-Min Liang
Summary: The photocatalytic decarboxylative radical addition bifunctionalization cascade presented in this study relies on single-electron transfer to complete the catalytic cycle. The reaction offers advantages such as the use of commercially available materials, wide functional group compatibility, and mild conditions. Importantly, some amino acids and bioactive carboxylic acids can provide corresponding products in moderate to good yields, highlighting their potential value in drug development.
Article
Chemistry, Multidisciplinary
Xuan Xiao, Yanxin Wang, Bing Liu, Zehui Zhang
Summary: In this study, a nitrogen-doped carbon encapsulated cobalt nanoparticle catalyst was discovered to be effective in catalyzing transfer hydrodeoxygenation reactions using formic acid as a hydrogen donor under mild conditions. The carbon layer protected the Co nanoparticles from the corrosive effects of formic acid, while the nitrogen atoms in the catalyst served as base sites to facilitate the transfer hydrogenation reactions of cobalt nanoparticles.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Applied
Bo Qu, Anjan Saha, Guisheng Li, Xingzhong Zeng, Xiaojun Wang, Nizar Haddad, Xiaowen Hou, Jon C. Lorenz, Lifen Wu, Scott Pennino, Heewon Lee, Jinhua J. Song, Chris H. Senanayake
Summary: This study describes a green and economical synthetic route for enantiomerically pure cis-4-amino-3-fluoro-1-methylpiperidine on a multikilogram scale. The synthesis involves a highly regio-, chemo-, and enantioselective asymmetric hydrogenation, resulting in the target compound with high yield and enantiomeric excess.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Physical
Risto Savela, Nataliya D. Shcherban, Marko M. Melander, Igor Bezverkhyy, Irina L. Simakova, Otto Langvik, Ekaterina Kholkina, Tamara Schindler, Annabelle Krauss, Karoliina Honkala, Dmitry Yu Murzin, Reko Leino
Summary: Selective hydrogenation of unsaturated imines over heterogeneous catalysts, specifically with iridium on carbon nitrides and amphoteric metal oxides in toluene solvent, provides the best selectivity towards unsaturated amines. This study demonstrates a promising catalytic performance and chemoselectivity, which has not been reported before, under atmospheric hydrogen pressure and low temperatures.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Biochemistry & Molecular Biology
Da Ke, Shaodong Zhou
Summary: In this study, an efficient nickel boride nanoclusters catalyst supported by a TS-1 molecular sieve was reported for the synthesis of amines. The catalyst showed high activity, simple preparation, and reusability, making it promising for industrial production of amines.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Inorganic & Nuclear
Cong Xu, Yu Feng, Faju Li, Jiahong Han, Yan-Mei He, Qing-Hua Fan
Article
Chemistry, Organic
Shanshan Zhang, Fei Chen, Yan-Mei He, Qing-Hua Fan
Article
Chemistry, Multidisciplinary
Ya Chen, Yixiao Pan, Yan-Mei He, Qing-Hua Fan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Organic
Li-Ren Wang, Dan Chang, Yu Feng, Yan-Mei He, Guo-Jun Deng, Qing-Hua Fan
Article
Chemistry, Organic
Yier Luo, Guanghui Ouyang, Yuping Tang, Yan-Mei He, Qing-Hua Fan
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Inorganic & Nuclear
Cong Xu, Yu Feng, Li-Ren Wang, Wen-Peng Ma, Yan-Mei He, Qing-Hua Fan
Article
Chemistry, Organic
Chenghao Li, Yixiao Pan, Yu Feng, Yan-Mei He, Youran Liu, Qing-Hua Fan
Article
Chemistry, Multidisciplinary
Qingqin Huang, Ya Chen, Xueting Zhou, Lei Dai, Yixin Lu
Summary: In this study, a highly efficient nickel-hydride-catalyzed reaction for the asymmetric synthesis of alkylcyclopropane scaffolds is reported. The method exhibits mild reaction conditions, broad applicability, and excellent functional group tolerance.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Chunlan Zhou, Haolin Zheng, Ya Chen, Guojiang Mao, Guo-Jun Deng
Summary: A metal-free four-component synthesis of tetrasubstituted pyrroles was developed using ammonium salt as the nitrogen source. This strategy involves [2 + 1 + 1 + 1] condensation to form the pyrrole ring in one pot. By utilizing 1,4-naphthoquinones and maleimides as versatile C2 fragments, substituted benzo[f]isoindole-4,9-diones and pyrrolo[3,4-c]pyrrole-1,3-diones were obtained. This work is notable for its use of ammonium salt as the nitrogen source, readily available starting materials, and multibond formation within a single operation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shuowen Wang, Zhuohao Chen, Shanping Chen, Wen Shao, Ya Chen, Guo-Jun Deng
Summary: This study presents a novel and selective synthesis method for polycyclic fused maleimides from easily available raw materials under metal-free conditions.
Article
Chemistry, Organic
Shuowen Wang, Zhi Huang, Ruitong Yang, Ya Chen, Wen Shao, Guojiang Mao, Guo-Jun Deng
Summary: A novel protocol for constructing multi-substituted 4-hydroxyisoindoline-1,3-diones through an I-2-mediated cascade reaction has been described. This metal-free process involves the formation of three C-C bonds and one C-O bond using easily available raw materials, resulting in highly functionalized maleimide-fused phenols with structural diversity in satisfactory yields.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Ya Chen, Kun Zhu, Qingqin Huang, Yixin Lu
Summary: The study presents a method for regiodivergent sulfonylarylation of 1,3-enynes via dual nickel and photoredox catalysis, offering diverse reaction pathways and the first example of merging nickel and photoredox catalysis for efficient and versatile difunctionalization of 1,3-enynes.
Article
Chemistry, Multidisciplinary
Ya Chen, Junjie Wang, Yixin Lu
Summary: In this study, we combine photoredox catalysis and copper catalysis for the first time to achieve radical 1,4-carbocyanations of 1,3-enynes. By utilizing alkyl N-hydroxyphthalimide esters as radical precursors, the mild and redox-neutral protocol shows broad substrate scope and remarkable functional group tolerance. This strategy enables the synthesis of diverse multi-substituted allenes with high chemo- and regio-selectivities, allowing late stage allenylation of natural products and drug molecules.
Article
Chemistry, Organic
Youran Liu, Fei Chen, Yan-Mei He, Chenghao Li, Qing-Hua Fan
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
