Naoki Noto, Yuya Tanaka, T. Koike
Aug 30, 2018
Citations
0
Influential Citations
41
Citations
Journal
ACS Catalysis
Abstract
Well-defined 9,10-bis(di(p-tert-butylphenyl)amino)anthracene serves as a photocatalyst for radical fluoroalkylation under visible light irradiation. The diarylamine (Donor)–anthracene (π conjugated system)–diarylamine (Donor) scaffolds are easily accessed by typical palladium-catalyzed cross-coupling protocols of the corresponding halogenated anthracenes with various lithium diarylamides. The anthracene-based photocatalyst exhibits high reducing power, leading to generation of versatile fluoroalkyl radicals such as tri- and difluoroethyl and tri- and difluoromethyl radicals from the corresponding electron-accepting precursors. Catalyst design strongly influences the absorption capability of visible light and stability toward redox stimuli. The detailed mechanistic studies on the metal-free photocatalytic amino-trifluoroethylation of styrene with diphenyl(2,2,2-trifluoroethyl)sulfonium trifluoromethanesulfonate suggest that the reaction proceeds via catalytic radical processes rather than radical chain pro...