title: Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate.
abstract: Organotrifluoroborates have emerged as an alternative to toxic and air- and moisture-sensitive organometallic species for the synthesis of functionalized aryl and heteroaryl compounds. It has been shown that the trifluoroborate moiety can be easily converted into a variety of different substituents in a late synthetic stage. In this paper, we disclose a mild, selective, and convenient method for the ipso-nitrosation of organotrifluoroborates using nitrosonium tetrafluoroborate (NOBF(4)). Aryl- and heteroaryltrifluoroborates were converted into the corresponding nitroso products in good to excellent yields. This method proved to be tolerant of a broad range of functional groups.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
authors.forename: Gary A
authors.initials: GA
authors.lastname: Molander
authors.forename: Livia N
authors.initials: LN
authors.lastname: Cavalcanti
mesh_terms: D001881:Borates / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009569:Nitric Oxide / Q000138:chemical synthesis* / Q000737:chemistry*; D015538:Nitrosation
chemical_list: D001881:Borates; D006571:Heterocyclic Compounds; C088437:nitrosonium tetrafluoroborate; D009569:Nitric Oxide