title: Anti-Markovnikov hydroamination of alkenes catalyzed by an organic photoredox system.
abstract: Herein we report a metal-free method for the direct anti-Markovnikov hydroamination of unsaturated amines. Irradiation of the amine substrates with visible light in the presence of catalytic quantities of easily synthesized 9-mesityl-10-methylacridinium tetrafluoroborate and thiophenol as a hydrogen-atom donor furnished the nitrogen-containing heterocycles with complete regiocontrol. Two examples of intermolecular anti-Markovnikov alkene hydroamination are also disclosed.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
authors.forename: Tien M
authors.initials: TM
authors.lastname: Nguyen
authors.forename: David A
authors.initials: DA
authors.lastname: Nicewicz
mesh_terms: D000166:Acridines / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D008027:Light; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D055668:Photochemical Processes; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C586111:9-mesityl-10-methylacridinium tetrafluoroborate; D000166:Acridines; D000475:Alkenes; D001881:Borates; D010636:Phenols; D013438:Sulfhydryl Compounds; C042983:thiophenol