Issue 11, 2024

Electrochemically dehydrogenative C(sp2)–H/S–H cross-coupling: efficient synthesis of ortho-aminophenyl thioglycoside derivatives

Abstract

We have developed an electro-mediated method for synthesizing aryl thioglycosides through intermolecular anodic oxidative cross-dehydrogenative C(sp2)–S bond coupling reactions involving (un)protected 1-thiosugars and anilines. This protocol is sustainable without the use of external transition-metal catalysts or additional oxidants employed in previous methods. It demonstrates a broader substrate scope concerning both 1-thiosugars and anilines. Furthermore, the reaction is applicable to the late-stage functionalization of drugs. Mechanistic studies using cyclic voltammetry and control experiments reveal that a radical cross coupling process is implicated in this transformation.

Graphical abstract: Electrochemically dehydrogenative C(sp2)–H/S–H cross-coupling: efficient synthesis of ortho-aminophenyl thioglycoside derivatives

Supplementary files

Article information

Article type
Research Article
Submitted
28 Jan 2024
Accepted
02 Apr 2024
First published
03 Apr 2024

Org. Chem. Front., 2024,11, 3041-3047

Electrochemically dehydrogenative C(sp2)–H/S–H cross-coupling: efficient synthesis of ortho-aminophenyl thioglycoside derivatives

L. Hu, L. Zhu, S. Zhang, Y. Guo, Y. Li, J. Zhu and L. Wu, Org. Chem. Front., 2024, 11, 3041 DOI: 10.1039/D4QO00171K

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