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Radical Fluorosulfonylation: Accessing Alkenyl Sulfonyl Fluorides from Alkenes
Author(s) -
Nie Xingliang,
Xu Tianxiao,
Song Jinshuai,
Devaraj Anandkumar,
Zhang Bolun,
Chen Yong,
Liao Saihu
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202012229
Subject(s) - sulfonyl , chemistry , radical , context (archaeology) , reagent , combinatorial chemistry , organic chemistry , paleontology , alkyl , biology
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 FSO 2 + ‐type reagents, a radical fluorosulfonylation reaction with a fluorosulfonyl radical (FSO 2 . ) 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 FSO 2 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.