title: 4-Position-Selective C-H Perfluoroalkylation and Perfluoroarylation of Six-Membered Heteroaromatic Compounds.
abstract: The first 4-position-selective C-H perfluoroalkylation and perfluoroarylation of six-membered heteroaromatic compounds were achieved using nucleophilic perfluoroalkylation and perfluoroarylation reagents. The regioselectivity was controlled by electrophilically activating the heteroaromatic rings, while sterically hindering the 2-position, with a sterically bulky borane Lewis acid. The reaction proceeded in good yield, even in gram scale, and by a sequential reaction without isolating the intermediates. This reaction could be applied to late-stage trifluoromethylation of a bioactive compound.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Nagase
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.|ERATO, Japan Science and Technology Agency (JST), Kanai Life Science Catalysis Project, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Yoichiro
authors.initials: Y
authors.lastname: Kuninobu
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.|ERATO, Japan Science and Technology Agency (JST), Kanai Life Science Catalysis Project, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Motomu
authors.initials: M
authors.lastname: Kanai
mesh_terms: D000478:Alkylation; D001880:Boranes / Q000737:chemistry; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D058116:Lewis Acids / Q000737:chemistry
chemical_list: D001880:Boranes; D006571:Heterocyclic Compounds; D006845:Hydrocarbons, Fluorinated; D007202:Indicators and Reagents; D058116:Lewis Acids; D005461:Fluorine