Visible-Light-Induced Nickel-Catalyzed Radical Cross-Couplings to Access α-Aryl-α-trifluoromethyl Alcohols
Feng Chen, Xiu‐Hua Xu, Lingling Chu, Feng‐Ling Qing
Abstract
A photochemically induced nickel-catalyzed radical cross-coupling of phthalimido trifluoroethanol with aryl bromides to furnish α-aryl-α-trifluoromethyl alcohols is reported. This reaction proceeds via a photoinduced charge transfer of an electron donor-acceptor complex between Hantzsch ester and phthalimido trifluoroethanol, followed by 1,2-hydrogen atom transfer, to generate the α-hydroxytrifluoroethyl radical for the cross-coupling of aryl bromides. No exogenous photocatalysts or stoichiometric metal reductants are required in this mild and operationally simple protocol. Broad substrate compatibility and excellent functional group tolerance are observed.
Topics & Concepts
ChemistryArylTrifluoromethylCatalysisPhotochemistryNickelFunctional groupCoupling reactionHydrogen atomCombinatorial chemistryOrganic chemistryGroup (periodic table)AlkylPolymerFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods