title: Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides.
abstract: The scope and mechanistic implications of the direct transformation of heterocyclic N-oxides to 2-trifluoromethyl-, and related perfluoroalkyl- and perfluoroaryl-substituted N-heterocycles has been studied. The reaction is effected by perfluoroalkyl- and perfluorophenyltrimethylsilane in the presence of strong base. In situ displacement of the para-fluoro substituent in the pentafluorophenyl ring and the methoxy group in 8-methoxyquinolines with additional nucleophiles allows for further site-selective refunctionalization of the N-heterocyclic products.
authors.affiliation: Department of Chemistry, University of Texas at San Antonio, San Antonio, Texas, USA. oleg.larionov@utsa.edu.
authors.forename: David E
authors.initials: DE
authors.lastname: Stephens
authors.forename: Gabriel
authors.initials: G
authors.lastname: Chavez
authors.forename: Martin
authors.initials: M
authors.lastname: Valdes
authors.forename: Monica
authors.initials: M
authors.lastname: Dovalina
authors.forename: Hadi D
authors.initials: HD
authors.lastname: Arman
authors.forename: Oleg V
authors.initials: OV
authors.lastname: Larionov
mesh_terms: D003497:Cyclic N-Oxides / Q000737:chemistry*; D005466:Fluorocarbons / Q000138:chemical synthesis* / Q000737:chemistry*; D007700:Kinetics; D008745:Methylation; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003497:Cyclic N-Oxides; D005466:Fluorocarbons; D012821:Silanes