Visible-Light-Induced Defluorinative α-C(sp<sup>3</sup>)–H Alkylation for the Synthesis of <i>gem</i>-Difluoroallylated α-Trifluoromethylamines
Bingran Chen, Qinlin Chen, Yang Liu, Jinxiu Chen, Xi Zhou, Haifeng Wang, Qiongjiao Yan, Wei Wang, Zeyu Cai, Fen‐Er Chen
Abstract
Herein, we describe a novel and efficient photoredox catalytic C α radical addition/defluoroalkylation coupling reaction between α-trifluoromethyl alkenes and N -trifluoroethyl hydroxylamine. A series of gem -difluoroallylated α-trifluoromethylamines were synthesized by the C α radical addition enabled by a 1,2-H shift of the in situ-generated N- trifluoroethyl radical. Notably, this protocol is distinguished by its mild conditions, easy operation, and excellent functional group tolerability.
Topics & Concepts
ChemistryHydroxylamineAlkylationTrifluoromethylFunctional groupCatalysisVisible spectrumMedicinal chemistryPhotoredox catalysisPhotochemistryCombinatorial chemistryOrganic chemistryPhotocatalysisPolymerPhysicsOptoelectronicsAlkylFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods