Organomediated electrochemical fluorosulfonylation of aryl triflates via selective C-O bond cleavage.

ABSTRACT: Although aryl triflates are essential building blocks in organic synthesis, the applications as aryl radical precursors are limited. Herein, we report an organomediated electrochemical strategy for the generation of aryl radicals from aryl triflates, providing a useful method for the synthesis of aryl sulfonyl fluorides from feedstock phenol derivatives under very mild conditions. Mechanistic studies indicate that key to success is to use catalytic amounts of 9, 10-dicyanoanthracene as an organic mediator, enabling to selectively active aryl triflates to form aryl radicals via orbital-symmetry-matching electron transfer, realizing the anticipated C-O bond cleavage by overcoming the competitive S-O bond cleavage. The transition-metal-catalyst-free protocol shows good functional group tolera

SUBMITTER: Kong X 

PROVIDER: S-EPMC10618246 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature