Regioselective C−H Trifluoromethylation and Its Related Reactions of (Hetero)aromatic Compounds

Abstract

Fluorinated functional groups, including trifluoromethyl group, play important roles in the development of drugs, agrochemicals, and organic functional materials. Therefore, the development of highly effective and practical reactions to introduce fluorinated functional groups into (hetero)aromatic compounds is highly desirable. We have achieved several regioselective C−H trifluoromethylation and related reactions by electrophilic and nucleophilic activation of six‐membered heteroaromatic compounds and steric protection of aromatic compounds. These reactions proceed in good to excellent yields, even on a gram scale, with high functional group tolerance, and are applicable to the regioselective trifluoromethylation of drug molecules. In this personal account, the background of the introduction reactions of fluorinated functional groups, our reaction designs to achieve regioselective C−H trifluoromethylation and the related reactions of (hetero)aromatic compounds are explained.

Harnessing photocatalytic and electrochemical approaches for C–H bond trifluoromethylation and fluoroalkylation

“…Alongside, several useful fluoroalkylation reactions were also developed under photo and electrochemical approaches. 25 Therefore, a concise overview encompassing the trifluoromethylation and fluoroalkylation of all types of C–H bonds, including C(sp 3 )–H, C(sp 2 )–H, and C(sp)–H bonds, through photoredox and electrochemical methods is crucial. Herein, we intend to provide a brief and essential summary on trifluoromethylation and fluoroalkylation reactions for functionalisation of different C–H bonds in various organic scaffolds through photocatalytic, electrochemical and electrophotocatalytic approaches and their typical mechanistic pathways.…”