Visible-Light-Mediated β-C–H <i>gem</i>-Difluoroallylation of Aldehydes and Cyclic Ketones through C–F Bond Cleavage of 1-Trifluoromethyl Alkenes
Devireddy Anand, Zhengchang Sun, Lei Zhou
Abstract
gem-Difluoroalkene bearing a carbonyl group is a challenging target to synthesize by conventional methods. Herein we report a mild and concise route to access the target compounds through the visible-light-mediated direct β-C–H gem-difluoroallylation of aliphatic aldehydes and cyclic ketones. Upon a synergistic combination of photoredox catalysis and organocatalysis, various α-CF3 alkenes were employed as the gem-difluoroallylation reagents via the C–F bond cleavage.
Topics & Concepts
ChemistryReagentTrifluoromethylCleavage (geology)CatalysisBond cleavageOrganocatalysisMedicinal chemistryVisible spectrumPhotochemistryCombinatorial chemistryOrganic chemistryEnantioselective synthesisGeotechnical engineeringPhysicsAlkylOptoelectronicsFracture (geology)EngineeringFluorine in Organic ChemistryRadical Photochemical Reactions