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Enantioselective Radical Carbocyanation of 1,3-Dienes via Photocatalytic Generation of Allylcopper Complexes

Fu-Dong Lu, Liang-Qiu Lu, Gui-Feng He, Jun-Chuan Bai and Wen-Jing Xiao*

*College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan 430079, China, Email: wxiaomail.ccnu.edu.cn

F.-D. Lu, L. Q. Lu, G.-F. He, J.-C. Bai, W.-J. Xiao, J. Am. Chem. Soc., 2021, 143, 4168-4173.

DOI: 10.1021/jacs.1c01260 (free Supporting Information)



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Abstract

By using synergetic photoredox/copper catalysis, a visible-light-induced, enantioselective carbocyanation of 1,3-dienes with carboxylic acid derivatives and trimethylsilyl cyanide is achieved under mild and neutral conditions. A diverse range of chiral allyl cyanides is produced in generally good efficiency and with high enantioselectivity from bench-stable and user-safe chemicals.


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proposed mechanism



Key Words

cyanation, alkylation, multicomponent reactions, photochemistry


ID: J48-Y2021