Gem-Difluoroallylation of Aryl Sulfonium Salts
Yue Zhao, Claire Empel, Wenjing Liang, René M. Koenigs, Frédéric W. Patureau
Abstract
The unprecedented photochemical late-stage defluorinative gem-difluoroallylation of aryl sulfonium salts, which are formed site-selectively by direct C(sp2)─H functionalization, is herein disclosed. This method is distinguished by its mild reaction conditions, wide scope, and excellent site-selectivity. As showcase examples, a Flurbiprofen and Pyriproxyfen derivatives could be late stage C(sp2)─H gem-difluoroallylated with high yields. Experimental and computational investigations were conducted.
Topics & Concepts
SulfoniumChemistryArylCombinatorial chemistrySelectivitySurface modificationSalt (chemistry)Organic chemistryCatalysisAlkylPhysical chemistryFluorine in Organic ChemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques