Photo-organocatalytic Synthesis of β-Keto Sulfonyl Fluorides via Radical Fluorosulfonylation of Vinyl Acetates
Peng Wang, Shaojie Li, Saihu Liao, Honghai Zhang, Na Yang
Abstract
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.
Topics & Concepts
ChemistrySulfonylKetoneMethyl vinyl ketoneAlkylArylOrganic chemistryOrganocatalysisPhotocatalysisCatalysisPhotoredox catalysisEnantioselective synthesisSulfur-Based Synthesis TechniquesFluorine in Organic ChemistryRadical Photochemical Reactions