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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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Source :
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN: 1433-7851
Year: 2020
Issue: 8
Volume: 60
Page: 3956-3960
1 5 . 3 3 6
JCR@2020
1 6 . 1 0 0
JCR@2023
ESI Discipline: CHEMISTRY;
ESI HC Threshold:160
JCR Journal Grade:1
CAS Journal Grade:2
Cited Count:
WoS CC Cited Count: 72
SCOPUS Cited Count: 68
ESI Highly Cited Papers on the List: 0 Unfold All
WanFang Cited Count:
Chinese Cited Count:
30 Days PV: 2
Affiliated Colleges: