Visible-Light-Driven C–H Imidation of Arenes and Heteroarenes by a Phosphonium Ylide Organophotoredox Catalyst: Application to C–H Functionalization of Alkenes
Yasunori Toda, Toya Kobayashi, Fumiya Hirai, Takamichi Yano, Makoto Oikawa, Kimiya Sukegawa, Masahiro Shimizu, Fuyuki Ito, Hiroyuki Suga
Abstract
Phosphonium ylide catalysis through an oxidative quenching cycle has been developed for visible-light-driven C-H imidation of arenes and heteroarenes. The present protocol could be applied not only to trihalomethylative lactonization reactions involving trifluoromethyl, trichloromethyl, and tribromomethyl radicals but also to the first example of an organophotoredox-catalyzed imidative lactonization reaction involving a nitrogen-centered electrophilic radical species.
Topics & Concepts
YlidePhosphoniumElectrophileCatalysisChemistryRadicalCatalytic cycleTrifluoromethylSurface modificationQuenching (fluorescence)Medicinal chemistryPhotochemistryOrganic chemistryAlkylPhysicsQuantum mechanicsPhysical chemistryFluorescenceRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry