Photo-organocatalytic Synthesis of β-Keto Sulfonyl Fluorides via Radical Fluorosulfonylation of Vinyl Acetates

Abstract

A metal-free synthesis of useful β-keto sulfonyl fluorides has been established via radical fluorosulfonylation of ketone-derived vinyl acetates under photoredox organocatalysis by using 1-fluorosulfonyl benzoimidazolium (FABI) as the fluorosulfonyl radical source and oxygen-doped anthanthrene (ODA) as the photocatalyst. A series of aryl and alkyl β-keto sulfonyl fluorides as well as cyclic analogues can be readily obtained in moderate to high yields from widely available ketone starting materials.

Key words

sulfonyl fluorides - radical fluorosulfonylation - vinyl acetates - photoredox - organocatalysis

Publication History

Received: 30 June 2022

Accepted after revision: 09 August 2022

Article published online:
09 September 2022

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