Issue 11, 2024

Light-promoted photocatalyst-free and redox-neutral hydrosulfonylation of unactivated alkenes using sulfinic acid

Abstract

A hydrosulfonylation reaction of unactivated alkenes with sulfinic acids was realized under light irradiation. This reaction features photocatalyst- and additive-free conditions. A diverse set of unactivated alkenes can be transformed into alkyl-substituted sulfones with good yields and anti-Markovnikov regioselectivity. The present protocol was amenable to gram-scale synthesis, as well as late-stage modification of drugs and natural products. Preliminary mechanistic studies on UV-visible light absorption suggested the key role of sulfinic acid as a light-absorbing species. DFT calculations also shed light on the mechanism of this reaction, which may involve a radical chain pathway.

Graphical abstract: Light-promoted photocatalyst-free and redox-neutral hydrosulfonylation of unactivated alkenes using sulfinic acid

Supplementary files

Article information

Article type
Paper
Submitted
25 Jan 2024
Accepted
16 Apr 2024
First published
19 Apr 2024

Green Chem., 2024,26, 6578-6583

Light-promoted photocatalyst-free and redox-neutral hydrosulfonylation of unactivated alkenes using sulfinic acid

Y. Song, C. Li, X. Hu, H. Zhang, Y. Mao, X. Wang, C. Wang, L. Hu and J. Yan, Green Chem., 2024, 26, 6578 DOI: 10.1039/D4GC00440J

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