Issue 20, 2023

Electrochemical synthesis of γ-keto sulfones containing a β-quaternary carbon center via 1,2-migration

Abstract

An effective electrochemical rearrangement reaction, both oxidant and metal catalyst-free, is presented to construct γ-keto sulfones containing a β-quaternary carbon center in this study. In the protocol, radicals are generated from benzenesulfonyl hydrazines, which cause 1,2-migrations of starting materials, 2-methylallyl alcohol derivatives, and formation of new C–C and C–S bonds. A series of aryl-migration, alkyl-migration and ring expansion products are obtained in good yields with excellent functional group tolerance. Gram-scale reaction demonstrates that the electro-oxidative rearrangement strategy has the potential for industrial practicability. Additionally, a possible and reasonable mechanism is proposed based on existing literature reports, control experiments and cyclic voltammograms.

Graphical abstract: Electrochemical synthesis of γ-keto sulfones containing a β-quaternary carbon center via 1,2-migration

Supplementary files

Article information

Article type
Paper
Submitted
15 jun 2023
Accepted
12 sep 2023
First published
13 sep 2023

Green Chem., 2023,25, 8273-8279

Electrochemical synthesis of γ-keto sulfones containing a β-quaternary carbon center via 1,2-migration

W. Xia, Y. Yang, X. Zhang, L. Hu and Y. Xiong, Green Chem., 2023, 25, 8273 DOI: 10.1039/D3GC02128A

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