title: Regioselective insertion of o-carborynes into the α-C-H bond of tertiary amines: synthesis of α-carboranylated amines.
abstract: o-Carboryne can undergo α-CH bond insertion with tertiary amines, thus affording α-carboranylated amines in very good regioselectivity and isolated yields. In this process, the nucleophilic addition of tertiary amines to the multiple bond of o-carboryne generates a zwitterionic intermediate. An intramolecular proton transfer, followed by a nucleophilic attack leads to the formation of the final product. Thus, regioselectivity is highly dependent upon the acidity of α-CH proton of tertiary amines. This approach serves as an efficient methodology for the preparation of a series of 1-aminoalkyl-o-carboranes.
authors.affiliation: Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong (China).
authors.forename: Da
authors.initials: D
authors.lastname: Zhao
authors.forename: Jiji
authors.initials: J
authors.lastname: Zhang
authors.forename: Zuowei
authors.initials: Z
authors.lastname: Xie
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000588:Amines
keywords: amines; boron; carborynes; lithium; regioselectivity