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Reductant-Free Enantioselective Aza-Reformatsky Reaction Enabled by Synergistic Visible Light Photocatalysis and Lewis Acid Catalysis.

作者信息

Jiang Mingyi, Yu Zengcheng, Yang Linhan, Wang Fei, Cao Weidi, Liu Xiaohua, Feng Xiaoming

机构信息

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.

Center for Natural Products Research, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610047, China.

出版信息

Angew Chem Int Ed Engl. 2025 Apr 17;64(17):e202500756. doi: 10.1002/anie.202500756. Epub 2025 Feb 28.

Abstract

Classical aza-Reformatsky reaction generally involves excess reductants. Herein, we developed a visible light-induced catalytic asymmetric aza-Reformatsky reaction via a chiral Lewis acid-assisted direct excitation of imines without additional reductants, enabling the carbon-iodine bond cleavage of iododifluoromethyl ketones and the subsequent enantioselective radical coupling. This protocol provided an ingenious access to chiral β-amino ketones containing a gem-difluorine moiety. The mechanistic studies including radical trapping experiment, NMR experiment, electron paramagnetic resonance experiment, cyclic voltammetry experiment and spectroscopic analysis rationalized the reaction process.

摘要

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