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Org Lett. 2019 Nov 1;21(21):8673-8678. doi: 10.1021/acs.orglett.9b03284. Epub 2019 Oct 22.

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

Author information

1
Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry , Fuzhou University , 2 Xueyuan Road , Fuzhou 350116 , P.R. China.
2
Beijing National Laboratory for Molecular Sciences (BNLMS) , Fuzhou University , Fuzhou 350116 , P.R. China.

Abstract

A visible-light-mediated deaminative thioesterification of amino acid derived Katritzky salts with thiobenzoic acid has been developed, which provides a novel synthetic method for the synthesis of 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, which represents a new entry for EDA complex chemistry.

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