title: Toward Efficient Nucleophilic Azaborine Building Blocks for the Synthesis of B-N Naphthyl (Hetero)arylmethane Isosteres.
abstract: To develop a method for the synthesis of a class of azaborines, potassium 2-(trifluoroboratomethyl)-2,1-borazaronaphthalenes have been synthesized to serve as nucleophilic building blocks. In palladium-catalyzed cross-coupling reactions with (hetero)aryl chlorides they serve to produce a variety of pseudobenzylic (hetero)aryl substituted azaborines. Potassium 2-(trifluoroboratomethyl)-2,1-borazaronaphthalenes are crystalline solids that are more stable than 2-(chloromethyl)-2,1-borazaronaphthalenes and have a broader substrate scope in cross-coupling reactions compared to their pseudobenzylic chloride counterparts.
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: Javad
authors.initials: J
authors.lastname: Amani
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
mesh_terms: D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000590897:2-chloro-2,1-borazaronaphthalene; D004952:Esters; D009281:Naphthalenes; D010165:Palladium