Issue 4, 2019

Intermolecular oxidative radical fluoroalkylfluorosulfonylation of unactivated alkenes with (fluoroalkyl)trimethylsilane, silver fluoride, sulfur dioxide and N-fluorobenzenesulfonimide

Abstract

An intermolecular oxidative radical fluoroalkylfluorosulfonylation reaction of unactivated alkenes with convenient and commercially available (fluoroalkyl)trimethylsilane, silver fluoride, sulfur dioxide and N-fluorobenzenesulfonimide (NFSI) is described. This transformation efficiently affords various fluoroalkyl-containing alkyl sulfonyl fluorides with good functional group tolerance under mild conditions. Silver fluoroalkyl complexes as the fluoroalkyl radical source generated from (fluoroalkyl)trimethylsilane and silver fluoride may be the key intermediate.

Graphical abstract: Intermolecular oxidative radical fluoroalkylfluorosulfonylation of unactivated alkenes with (fluoroalkyl)trimethylsilane, silver fluoride, sulfur dioxide and N-fluorobenzenesulfonimide

Supplementary files

Article information

Article type
Research Article
Submitted
03 nov 2018
Accepted
16 dec 2018
First published
19 dec 2018

Org. Chem. Front., 2019,6, 447-450

Intermolecular oxidative radical fluoroalkylfluorosulfonylation of unactivated alkenes with (fluoroalkyl)trimethylsilane, silver fluoride, sulfur dioxide and N-fluorobenzenesulfonimide

Q. Lin, Y. Liu, Z. Xiao, L. Zheng, X. Zhou, Y. Guo, Q. Chen, C. Zheng and C. Liu, Org. Chem. Front., 2019, 6, 447 DOI: 10.1039/C8QO01192C

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