Iron-Catalyzed Dehydrogenative Borylation of Terminal Alkynes

被引：35
|
作者：
Wei, Duo [1 ]
Carboni, Bertrand [1 ]
Sortais, Jean-Baptiste [1 ,2 ,3 ]
Darcel, Christophe [1 ]
机构：
[1] Univ Rennes, CNRS, ISCR, UMR 6226, F-35042 Rennes, France
[2] Univ Toulouse, CNRS, LCC, UPS, Toulouse, France
[3] Inst Univ France, 1 Rue Descartes, F-75231 Paris 05, France
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 19期
关键词：
Iron; alkyne; dehydrogenative borylation; pinacolborane; alkynylboronates; C-H BORYLATION; MARKOVNIKOV-SELECTIVE HYDROBORATION; CROSS-COUPLING REACTIONS; ALKENE HYDROBORATION; METAL; FUNCTIONALIZATION; VINYLARENES; COMPLEXES; BONDS; 1,4-HYDROBORATION;
D O I：
10.1002/adsc.201800588
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The catalytic system based on Fe(OTf)(2) (2.5 mol%) and DABCO (1 mol%) selectively promotes the dehydrogenative borylation of both aromatic and aliphatic terminal alkynes to afford alkynylboronate derivatives in the presence of 1 equiv. of pinacolborane at 100 degrees C in toluene. This methodology is applicable to a variety of terminal alkynes (16 examples, yield: 62-93%).
引用
收藏
页码：3649 / 3654
页数：6
相关论文
共 50 条
  • [1] ZnBr2-Catalyzed Dehydrogenative Borylation of Terminal Alkynes
    Luo, Man
    Qin, Yi
    Chen, Xi
    Xiao, Qian
    Zhao, Binlin
    Yao, Weiwei
    Ma, Mengtao
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 16666 - 16674
  • [2] Copper-catalyzed dehydrogenative borylation of terminal alkynes with pinacolborane
    Romero, Erik A.
    Jazzar, Rodolphe
    Bertrand, Guy
    CHEMICAL SCIENCE, 2017, 8 (01) : 165 - 168
  • [3] Iron-Catalyzed Vinylzincation of Terminal Alkynes
    Huang, Qiang
    Su, Yu-Xuan
    Sun, Wei
    Hu, Meng-Yang
    Wang, Wei-Na
    Zhu, Shou-Fei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (01) : 515 - 526
  • [4] Iron-Catalyzed Alkylzincation of Terminal Alkynes
    Huang, Qiang
    Su, Yu-Xuan
    Sun, Wei
    Hu, Meng-Yang
    Wang, Wei-Na
    Zhu, Shou-Fei
    ACS CATALYSIS, 2022, 12 (04): : 2581 - 2588
  • [5] Iron-Catalyzed E-Selective Dehydrogenative Borylation of Vinylarenes with Pinacolborane
    Wang, Chao
    Wu, Caizhi
    Ge, Shaozhong
    ACS CATALYSIS, 2016, 6 (11): : 7585 - 7589
  • [6] Kinetic investigation of the dehydrogenative borylation of terminal alkynes
    Foley, Bryan
    Bhuvanesh, Nattamai
    Ozerov, Oleg
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [7] Selective iron-catalyzed transfer hydrogenation of terminal alkynes
    Wienhoefer, Gerrit
    Westerhaus, Felix A.
    Jagadeesh, Rajenahally V.
    Junge, Kathrin
    Junge, Henrik
    Beller, Matthias
    CHEMICAL COMMUNICATIONS, 2012, 48 (40) : 4827 - 4829
  • [8] Iron-Catalyzed Oxyalkylation of Terminal Alkynes with Alkyl Iodides
    Deng, Weili
    Ye, Changqing
    Li, Yajun
    Li, Daliang
    Bao, Hongli
    ORGANIC LETTERS, 2019, 21 (01) : 261 - 265
  • [9] Cyclic (alkyl) (amino) carbene copper (I) catalyzed dehydrogenative borylation and α-hydroboration of terminal alkynes
    Romero, Erik
    Jazzar, Rodolphe
    Bertrand, Guy
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [10] Iron-Catalyzed Oxidative Coupling of Terminal Alkynes with Arylboronic Acids
    You, Xiu L.
    Xu, Lai
    Hu, Tao
    LETTERS IN ORGANIC CHEMISTRY, 2012, 9 (04) : 300 - 304
12345