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Asymmetric Access of γ-Amino Acids and γ-Amino Phosphonic Acid Derivatives via Copper-Catalyzed Enantioselective and Regioselective hydroamination

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CCS Chemistry 2022年第6期4卷 1901-1911页

作者： Zhiping Yang Qingwei Du Yanxin Jiang Jun(Joelle) Wang Harbin Institute of Technology Harbin 150001 Department of Chemistry Southern University of Science and Technology(SUSTech)Shenzhen 518055 Department of Chemistry Hong Kong Baptist UniversityKowloonHong Kong 999077

γ-Aminobutyric acid is a major inhibitory neurotransmitter in the mammalian central nervous system that plays a substantial role in brain disorders.γ-Amino phosphonic acid is a unique surrogate of both natural and unnatural γ-amino acid.Because of their unique biological activity,γ-amino acid and γ-amino phosphonic acid derivatives have attracted considerable attention.However,an efficient and straightforward method for constructing chiral γ-substituted-γ-amino acid and γ-amino phosphonic acid derivatives remains a long-standing challenge.Herein,a highly efficient,versatile,and universal Cucatalyzed asymmetric hydroamination of cinnamyl esters,cinnamyl phosphonates,and cinnamyl phosphine oxides is presented for accessing γ-amino acid andγ-amino phosphonic acid derivatives in good yields with high levels of enantiocontrol and regioselectivity.

关键词： asymmetric catalysis copper hydroamination γ-amino acid amino phosphine

An Efficient and Green Approach to Synthesizing Enamines by Intermolecular hydroamination of Activated Alkynes

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Chemical Research in Chinese Universities 2015年第2期31卷 212-217页

作者： ZENG Ruijie SHENG Hongting RAO Bo FENG Yan WANG Hao SUN Yehua CHEN Man ZHU Manzhou School of Chemistry and Chemical Engineering Anhui University Hefei 230601 P. R. China

An efficient, atom-economic and green approach to synthesizing enamines was developed by intermolecular hydroamination of activated alkynes with high yields under catalyst- and solvent-free conditions. β-Dimethylamino-acrylate derivatives were also obtained with high yields. In the synthetic process of the derivatives, N,N-dimethylformamide（DMF） pretreated with metal Na, was used as reactant instead of dimethylamine gas. The proposed synthetic method can be used for the synthesis of （E）-ethyl-3-（dimethylamino）acrylate（3cl）, and provide a new possible way to the synthesis of Quinolones.

关键词： Enamine hydroamination Activated alkyne Catalyst-free Solvent-free N,N-Dimethylformamide

Visible-light-driven hydroamination of Alkynes over a New Type of Activated Carbon Immobilized Cu^(2+)Photocatalyst

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Chemical Research in Chinese Universities 2020年第6期36卷 1039-1044页

作者： GU Xianmo MA Pengwei LIU Pei WANG Ruiyi LI Xincheng ZHENG Zhanfeng State Key Laboratory of Coal Conversion Institute of Coal ChemistryChinese Academy of SciencesTaiyuan 030001P.R.China Center of Materials Science and Optoelectronics Engineering University of Chinese Academy of SciencesBeijing 100049P.R.China

A new type of activated carbon immobilized copper(Cu/AC)photocatalyst was prepared by a facile impregnation-adsorption method,where Cu^2+is chemically adsorbed by abundant oxygenated functional groups on large-surface-area activated carbon surface.Cu/AC exhibited good activity and selectivity to imine for the hydroamination of alkynes at 60℃under visible light irradiation.The reaction is initialized by the activation of alkynes molecules at Cu active sites with the aid of light as evidenced by the solid-state NMR and laser photolysis measurements and the control experiments.This strategy for catalyst design is potentially extended to the immobilization of other metal homogeneous catalysts for various heterogeneous catalytic systems.

关键词： Activated carbon Copper hydroamination Photocatalysis

Origins of catalyst-controlled enantiodivergent hydroamination of enones with pyridazinones:A computational study

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Chinese Chemical Letters 2021年第9期32卷 2769-2772页

作者： Xiangwei Ren Hongli Wu Mei Zhang Wentao Zhao Genping Huang Department of Chemistry School of Science and Tianjin Key Laboratory of Molecular Optoelectronic SciencesTianjin UniversityTianjin 300072China

Density functional theory calculations have been performed to investigate the dipeptide phosphinecatalyzed hydroamination of enones with pyridazinones.The computations reveal that a number of the N-H...O hydrogen-bonding interactions with the pyridazinone moiety and the C–H...O hydrogenbonding interactions with the enone moiety are present in the enantioselectivity-determining Michael addition transition states.The experimentally-observed catalyst-controlled enantiodivergence is mainly attributed to the significant impact of the substituent of the amide moiety of the dipeptide phosphine on the relative strength of the N-H...O hydrogen-bonding interactions,which was found to affect the Si face attack transition state,enabling the enantioselectivity switch upon change of chiral dipeptide phosphine catalyst.

关键词： Dipeptide phosphine catalyst hydroamination Mechanism Selectivity DFT calculations

Cobalt-Catalyzed Difunctionalization of Styrenes via Ligand Relay Catalysis

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Chinese Journal of Chemistry 2023年第24期41卷 3633-3638页

作者： Bingcheng Wang Yufeng Sun Zhan Lu Department of Chemistry Zhejiang UniversityHangzhouZhejiang310058 China College of Chemistry Zhengzhou UniversityZhengzhouHenan450001 China

Here,we report a cobalt-catalyzed sequential dehydrogenative Heck silylation/hydroamination of styrenes with hydrosilane and diazo compound to access 1-amino-2-silyl compounds with excellent regioselectivity.This difunctionalization reaction could undergo smoothly using 1 mol%catalyst loading with good functional group tolerance.Not only di-and tri-substituted hydrosilanes,but also alkoxysilane is suitable,which does explore the scope of the family of 1-amino-2-silyl compounds.The ligand relay phenomenon between neutral tridentate NNN ligand and anionic NNN ligand is observed for the first time via absorption spectral analysis in this one-pot,two-step transformations.The primary mechanism has been proposed based on the control experiments.

关键词： Ligand relay catalysis Difunctionalization Styrene Alkoxysilane hydroamination Diazo compounds

Titanium complexes supported by pyrrolyl ligand as catalysts for hydroamination and polymerization reactions,and as antitumor reagent

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Titanium complexes supported by pyrrolyl ligand as catalysts...