title: Accessing an azaborine building block: synthesis and substitution reactions of 2-chloromethyl-2,1-borazaronaphthalene.
abstract: One major synthetic route to the synthesis of benzyl amines, ethers, and esters is the nucleophilic substitution of a benzylic halide. To develop a method for the facile synthesis and functionalization of the isosteric azaborines, 2-chloromethyl-2,1-borazaronaphthalene has been synthesized in one step to afford a similar common precursor to a benzylic halide. This B-N isostere has been shown to be an effective building block by serving as an electrophile in substitution reactions with a large variety of nucleophiles.
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
authors.forename: Javad
authors.initials: J
authors.lastname: Amani
mesh_terms: D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C000594865:2-chloromethyl-2,1-borazaronaphthalene; D001593:Benzyl Compounds; D006846:Hydrocarbons, Halogenated; D009281:Naphthalenes