title: Accessing 2,1-borazaronaphthols: self-arylation of 1-alkyl-2-aryl-3-bromo-2,1-borazaronaphthalenes.
abstract: Unlike their B-alkyl counterparts, brominated N-alkyl B-aryl 2,1-borazaronaphthalenes undergo a self-arylation reaction in the presence of a catalytic amount of palladium and base, in which the azaborine serves as both the electrophile and the nucleophile. The products of the self-arylation are air- and moisture-stable 2,1-borazaronaphthols, previously only observed in basic alcoholic solvents. The steric encumbrance of the azaborine appears to prevent formation of the corresponding boron acid anhydride, allowing access to a family of 2,1-borazaronaphthol derivatives.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Gary A
authors.initials: GA
authors.lastname: Molander
authors.forename: Steven R
authors.initials: SR
authors.lastname: Wisniewski
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D009284:Naphthols / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry
chemical_list: C556261:1,2-azaborine; D001896:Boron Compounds; D009281:Naphthalenes; D009284:Naphthols; D010165:Palladium