Chemo- and Site-Selective Electro-Oxidative Alkane Fluorination by C(sp3 )-H Cleavage

Chemistry. 2022 Oct 26;28(60):e202201654. doi: 10.1002/chem.202201654. Epub 2022 Aug 31.

Abstract

Electrochemical fluorinations of C(sp3 )-H bonds with a nucleophilic fluoride source have been accomplished in a chemo- and site-selective fashion, avoiding the use of electrophilic F+ sources and stoichiometric oxidants. The introduced metal-free strategy exhibits high functional group tolerance, setting the stage for late-stage fluorinations of biorelevant motifs. The synthetic utility of the C(sp3 )-H fluorination was reflected by subsequent one-pot arylation of the generated benzylic fluorides.

Keywords: C(sp3)−H functionalization; electrosynthesis; fluoride source; fluorination.