Dual-Role Catalysis by Thiobenzoic Acid in Cα–H Arylation under Photoirradiation
Fumihisa Kobayashi, Masashi Fujita, Takafumi Ide, Yuta Ito, Kenji Yamashita, Hiromichi Egami, Yoshitaka Hamashima
Abstract
Thiobenzoic acid (TBA) can serve as a single-electron reducing agent under photoirradiation from a blue light-emitting diode, in the presence of appropriate electron acceptors, and the resulting sulfur-centered radical species undergoes hydrogen atom abstraction. This dual-role catalysis by TBA enables regioselectivie Cα–H arylation of benzylamines, benzyl alcohols, and ethers, as well as dihydroimidazoles, with cyano(hetero)arenes in good yield, without the need for a transition-metal photocatalyst and/or synthetically elaborated organic dyes.
Topics & Concepts
ChemistryCatalysisPhotochemistryYield (engineering)PhotocatalysisDual roleSulfurPhotoredox catalysisHydrogen atom abstractionCombinatorial chemistryQuantum yieldHydrogen atomOrganic chemistryHydrogenAlkylFluorescenceMaterials scienceMetallurgyQuantum mechanicsPhysicsRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods