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Hantzsch Ester-Mediated Visible-Light-Induced Radical Ethoxycarbonyldifluoromethylation of Aryl Alkynes: Kinetic-Controlled Stereoselective Synthesis of Z-gem-Difluoroallyl Esters

Jian Hao*, Wanjun Ding, Zhichun Zheng, Linan Sun, Junjie Dong, Minjie Li* and Wen Wan*

*Department of Chemistry, Shanghai University, Shanghai 200444, China, Email: jhaoshu.edu.cn, minjielishu.edu.cn, wanwenshu.edu.cn

J. Hao, W. Ding, Z. Zheng, L. Sun, J. Dong, M. Li, W. Wan, J. Org. Chem., 2022, 87, 13750-13756.

DOI: 10.1021/acs.joc.2c01537


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Abstract

A kinetic-controlled photocatalyst-free visible-light-induced stereoselective synthesis of synthetically important α,α-gem-difluoro-Z-allyl esters was succeeded at room temperature in good yields and excellent Z-selectivity through a reductive radical ethoxycarbonyldifluoromethylation of terminal aryl alkynes with blue LED (465 nm)-excited Hantzsch ester.

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proposed mechanism



Key Words

fluoroalkanes, esters, Hantzsch ester, photochemistry


ID: J42-Y2022