Hydroboration of Arynes with N-Heterocyclic Carbene Boranes

被引：40
|
作者：
Taniguchi, Tsuyoshi [1 ]
Curran, Dennis P. [2 ]
机构：
[1] Kanazawa Univ, Sch Pharmaceut Sci, Inst Med Pharmaceut & Hlth Sci, Kanazawa, Ishikawa 9201192, Japan
[2] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 48期
基金：
美国国家科学基金会;
关键词：
arynes; boranes; hydroboration; main-group chemistry; N-heterocyclic carbenes; CROSS-COUPLING REACTIONS; CARBON-CARBON; ALKENES; BONDS; REDUCTIONS; BORYLATION; ALKYNES;
D O I：
10.1002/anie.201408345
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Arynes were generated in situ from ortho-silyl aryl triflates and fluoride ions in the presence of stable N-heterocyclic carbene boranes (NHC-BH3). Spontaneous hydroboration ensued to provide stable B-aryl-substituted NHC-boranes (NHC-BH2Ar). The reaction shows good scope in terms of both the NHC-borane and aryne components and provides direct access to mono-and disubstituted NHC-boranes. The formation of unusual ortho regioisomers in the hydroboration of arynes with an electron-withdrawing group supports a hydroboration process with hydride-transfer character.
引用
收藏
页码：13150 / 13154
页数：5
相关论文
共 50 条
  • [41] Giant N-heterocyclic carbene-containing macrocycles for cobalt-catalysed hydroboration of alkynes
    Zhang, Guoqi
    CHEMICAL COMMUNICATIONS, 2022, 58 (58) : 8109 - 8112
  • [42] A tropylium annulated N-heterocyclic carbene
    Appel, Sebastian
    Brueggemann, Peter
    Ganter, Christian
    CHEMICAL COMMUNICATIONS, 2020, 56 (63) : 9020 - 9023
  • [43] N-heterocyclic carbene adducts of carborane
    Willans, Charlotte E.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [44] N-heterocyclic carbene:: a versatile organocatalyst
    Sun, Xiao-Yu
    Wu, Jie
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (06) : 745 - 756
  • [45] Are There Carbenes in N-Heterocyclic Carbene Organocatalysis?
    Gehrke, Sascha
    Holloczki, Oldamur
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (51) : 16395 - 16398
  • [46] Oxidative N-Heterocyclic Carbene Catalysis
    De Risi, Carmela
    Brandolese, Arianna
    Di Carmine, Graziano
    Ragno, Daniele
    Massi, Alessandro
    Bortolini, Olga
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (04)
  • [47] A persistent P,N-heterocyclic carbene
    Frey, Guido D.
    Song, Maoying
    Bourg, Jean-Baptiste
    Donnadieu, Bruno
    Soleilhavoup, Michele
    Bertrand, Guy
    CHEMICAL COMMUNICATIONS, 2008, (39) : 4711 - 4713
  • [48] Syntheses of N-heterocyclic carbene precursors
    Burgess, Kevin
    CHEMISTRY & INDUSTRY, 2008, (12) : 27 - 27
  • [49] Chemistry of N-Heterocyclic Carbene Ligands
    Jahnke, Mareike C.
    Hahn, F. Ekkehardt
    TRANSITION METAL COMPLEXES OF NEUTRAL ETA1-CARBON LIGANDS, 2010, 30 : 95 - +
  • [50] N-Heterocyclic Carbene Catalyzed Transformylation
    Fernando, Jared E. M.
    Levens, Alison
    Moock, Daniel
    Lupton, David W.
    SYNTHESIS-STUTTGART, 2017, 49 (15): : 3505 - 3510
12345