title: Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.
abstract: Potassium vinyltrifluoroborate was found to be an efficient partner with benzamide derivatives for Rh(III)-catalyzed annulations. 4-Trifluoroboratotetrahydroisoquinolones were generated under mild conditions, affording a regioisomerically complementary substitution pattern to other alkenes in related reactions. These new boron-containing building blocks were derivatized by N-arylations, retaining the boron substituent for further elaboration.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Marc
authors.initials: M
authors.lastname: Presset
authors.forename: Daniel
authors.initials: D
authors.lastname: Oehlrich
authors.forename: Frederik
authors.initials: F
authors.lastname: Rombouts
authors.forename: Gary A
authors.initials: GA
authors.lastname: Molander
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001549:Benzamides / Q000737:chemistry*; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001549:Benzamides; D006845:Hydrocarbons, Fluorinated; D007546:Isoquinolines; D009942:Organometallic Compounds; C541327:potassium vinyltrifluoroborate; D012238:Rhodium