title: Facile Synthesis of N-Carboranyl Amines through an ortho-Carboryne Intermediate.
abstract: The efficient o-carboryne precursor 1-Li-2-OTf-o-C2 B10 H10 reacts with lithium amides at room temperature to give a series of N-carboranyl amines in moderate to high isolated yields. This reaction is compatible with a broad substrate scope from primary to secondary, alkyl to aryl amines. The reaction mechanism is also proposed on the basis of experimental results and DFT calculations. This represents the first general and efficient method for the synthesis of 1-NR(1) R(2) -o-carboranes.
authors.affiliation: Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Ruofei
authors.initials: R
authors.lastname: Cheng
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: Jie
authors.initials: J
authors.lastname: Zhang
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: Jiji
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. qiuzz@sioc.ac.cn.
authors.forename: Zaozao
authors.initials: Z
authors.lastname: Qiu
authors.affiliation: Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. zxie@cuhk.edu.hk.|Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong, China. zxie@cuhk.edu.hk.
authors.forename: Zuowei
authors.initials: Z
authors.lastname: Xie
keywords: addition reaction; amination; boron cluster; carborane; carboryne