title: Simple and Clean Photoinduced Aromatic Trifluoromethylation Reaction.
abstract: We describe a simple, metal- and oxidant-free photochemical strategy for the direct trifluoromethylation of unactivated arenes and heteroarenes under either ultraviolet or visible light irradiation. We demonstrated that photoexcited aliphatic ketones, such as acetone and diacetyl, can be used as promising low-cost radical initiators to generate CF3 radicals from sodium triflinate efficiently. The broad utility of this strategy and its benefit to medicinal chemistry are demonstrated by the direct trifluoromethylation of unprotected bidentate chelating ligand, xanthine alkaloids, nucleosides, and related antiviral drug molecules.
authors.affiliation: Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.|Department of Electrical and Computer Engineering, McGill University , 3480 University Street, Montreal, Quebec H3A 0E9, Canada.
authors.forename: Lu
authors.initials: L
authors.lastname: Li
authors.affiliation: Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.
authors.forename: Xiaoyue
authors.initials: X
authors.lastname: Mu
authors.affiliation: Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.
authors.forename: Wenbo
authors.initials: W
authors.lastname: Liu
authors.affiliation: Department of Electrical and Computer Engineering, McGill University , 3480 University Street, Montreal, Quebec H3A 0E9, Canada.
authors.forename: Yichen
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Department of Electrical and Computer Engineering, McGill University , 3480 University Street, Montreal, Quebec H3A 0E9, Canada.
authors.forename: Zetian
authors.initials: Z
authors.lastname: Mi
authors.affiliation: Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.
authors.forename: Chao-Jun
authors.initials: CJ
authors.lastname: Li
mesh_terms: D000096:Acetone / Q000737:chemistry; D000470:Alkaloids / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry; D002614:Chelating Agents / Q000737:chemistry; D005617:Chlorofluorocarbons, Methane / Q000138:chemical synthesis* / Q000737:chemistry; D003931:Diacetyl / Q000737:chemistry; D055772:Green Chemistry Technology / Q000379:methods; D006841:Hydrocarbons, Aromatic / Q000737:chemistry* / Q000528:radiation effects*; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry; D008024:Ligands; D008027:Light; D055668:Photochemical Processes; D014466:Ultraviolet Rays
chemical_list: D000470:Alkaloids; D000998:Antiviral Agents; D002614:Chelating Agents; D005617:Chlorofluorocarbons, Methane; D006841:Hydrocarbons, Aromatic; D007202:Indicators and Reagents; D007659:Ketones; D008024:Ligands; D000096:Acetone; D003931:Diacetyl; C009554:fluoroform