A general and efficient approach to various aliphatic sulfonyl fluorides by the reductive decarboxylative fluorosulfonylation of aliphatic carboxylic acids via a radical sulfur dioxide insertion and fluorination strategy was developed.
28 September 2021 in Organic & Biomolecular Chemistry
This paper reports a convenient copper-catalyzed three-component conversion of arylhydrazine hydrochlorides to arenesulfonyl fluorides in good yields under mild conditions, using 1,4-diazabicyclo [2.2.2]octane bis(sulfur dioxide) (DABSO) as a sulfonyl source and N-fluorobenzenesulfonimide (NFSI) as a fluorine source based on a radical sulfur dioxide insertion and fluorination strategy. Notably, arylhydrazine hydrochloride is used as a safe precursor of aryl radicals.
A palladium-catalyzed fluorosulfonylation reaction of aryl thianthrenium salts was developed to efficiently produce diverse aryl sulfonyl fluorides in moderate to good yieldsviaa radical sulfur dioxide insertion and fluorination strategy.
An efficient metal-free visible-light-mediated protocol for the synthesis of various aryl sulfonyl fluorides from diaryliodonium salts via a radical sulfur dioxide insertion and fluorination strategy was developed.