Radical Fluorosulfonylation: Accessing Alkenyl Sulfonyl Fluorides from Alkenes.

Angewandte Chemie
Xingliang NieSaihu Liao

Abstract

Sulfonyl fluorides have widespread applications in many fields. In particular, their unique biological activity has drawn considerable research interest in the context of chemical biology and drug discovery in the past years. Therefore, new and efficient methods for the synthesis of sulfonyl fluorides are highly in demand. In contrast to extensive studies on FSO2 + -type reagents, a radical fluorosulfonylation reaction with a fluorosulfonyl radical (FSO2 . ) remains elusive so far, probably owing to its instability and difficulty in generation. Herein, the development of the first radical fluorosulfonylation of alkenes based on FSO2 radicals generated under photoredox conditions is reported. This radical approach provides a new and general access to alkenyl sulfonyl fluorides, including structures that would otherwise be challenging to synthesize with previously established cross-coupling methods. Moreover, extension to the late-stage fluorosulfonylation of natural products is also demonstrated.

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Citations

Jun 24, 2021·Organic & Biomolecular Chemistry·Zai-Wei ZhangHaolin Tang
Jun 15, 2021·ACS Catalysis·Cayo LeeNicholas D Ball
Aug 6, 2021·Chemical Science·Tao ZhongJiang Weng
Sep 14, 2021·The Journal of Organic Chemistry·Fang-Fang FengDominique Cahard

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