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Visible-Light-Induced Deaminative Thioesterification of Amino Acid Derived Katritzky Salts via Electron Donor-Acceptor Complex Formation

Mingcheng Yang, Tianpeng Cao, Tianxiao Xu and Saihu Liao*

*Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, 2 Xueyuan Road, Fuzhou 350116, P.R. China, Email: shliaofzu.edu.cn

M. Yang, T. Cao, T. Xu, S. Liao, Org. Lett., 2019, 21, 8673-8678.

DOI: 10.1021/acs.orglett.9b03284


Abstract

A visible-light-mediated deaminative thioesterification of amino acid derived Katritzky salts with thiobenzoic acid provides α-mercapto acid derivatives under mild conditions. This photoredox catalyst-free generation of alkyl radicals via C-N bond cleavage is enabled by the formation of an electron-donor-acceptor (EDA) complex between the Katritzky salt and thiobenzoic acid anion.


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proposed mechanism



Key Words

photochemistry, thioesters


ID: J54-Y2019