Photocatalytic Hydro Tri/Difluoromethylation of Alkenes with Bench Stable Tri/Difluoromethylating Reagents
Girish Suresh Yedase, Munaifa Arif, Rositha Kuniyil, Veera Reddy Yatham
Abstract
Herein, we demonstrate the synthesis and characterization of bench stable tri/difluoromethylating reagents and their potential applications in redox neutral hydro tri/difluoromethylation of alkenes enabled by visible light. The new tri/difluoromethylating reagents are obtained on a gram-scale through simply cyclocondensation of commercially available anthranilamide with phenyltrifluoro or difluoromethyl ketone. Preliminary mechanistic studies indicated that a canonical photoredox catalytic cycle is being operative. DFT studies support this and further reveal that deprotonation occurs before radical cleavage. DFT studies also show that the better yield with HCF 2 reagent is attributed to the favorable expulsion of the corresponding radical moiety.