Copper as a Powerful Catalyst in the Direct Alkynylation of Azoles

被引：170
|
作者：
Besselievre, Francois [1 ]
Piguel, Sandrine [1 ]
机构：
[1] Ctr Univ Orsay, Inst Curie, UMR 176, CNRS, F-91405 Orsay, France
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 50期
关键词：
alkynes; alkynylation; C-H activation; copper; heterocycles; C-H BONDS; GACL3-CATALYZED ORTHO-ETHYNYLATION; DIRECT ARYLATION; HETEROAROMATIC-COMPOUNDS; ARYL BROMIDES; N-ARYLATION; PALLADIUM; HETEROARENES; HETEROCYCLES; OXAZOLES;
D O I：
10.1002/anie.200904776
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
[Chemical equation presented] Copper-bottomed catalysis! The direct alkynylation of azoles through a copper-based C - H bond activation, using alkynylbromides as the coupling partner, has been developed (see scheme). The method is very rapid, is functional-group tolerant, and provides a straightforward entry to diverse alkynyl heterocycles that is complementry to the Sonogashira reaction. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：9553 / 9556
页数：4
相关论文
共 50 条
  • [1] Nickel-Catalyzed Direct Alkynylation of Azoles with Alkynyl Bromides
    Matsuyama, Naoto
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    ORGANIC LETTERS, 2009, 11 (18) : 4156 - 4159
  • [2] 1,1-Dibromo-1-alkenes as Valuable Partners in the Copper-Catalyzed Direct Alkynylation of Azoles
    Berciano, Beatriz Pacheco
    Lebrequier, Sabrina
    Besselievre, Francois
    Piguel, Sandrine
    ORGANIC LETTERS, 2010, 12 (18) : 4038 - 4041
  • [3] Nickel- and Copper-Catalyzed Direct Alkynylation of Azoles and Polyfluoroarenes with Terminal Alkynes under O2 or Atmospheric Conditions
    Matsuyama, Naoto
    Kitahara, Masanori
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    ORGANIC LETTERS, 2010, 12 (10) : 2358 - 2361
  • [4] Highly Efficient and Versatile Pd-Catalyzed Direct Alkynylation of Both Azoles and Azolines
    Kim, Seok Hwan
    Chang, Sukbok
    ORGANIC LETTERS, 2010, 12 (08) : 1868 - 1871
  • [5] Room-Temperature Direct Alkynylation of Arenes with Copper Acetylides
    Theunissen, Cedric
    Evano, Gwilherm
    ORGANIC LETTERS, 2014, 16 (17) : 4488 - 4491
  • [6] Copper-catalyzed direct thiolation of azoles with aliphatic thiols
    Zhou, An-Xi
    Liu, Xue-Yuan
    Yang, Ke
    Zhao, Shu-Chun
    Liang, Yong-Min
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (15) : 5456 - 5462
  • [7] Copper catalyzed/mediated direct B–H alkenylation/alkynylation in carboranes
    Yu Chen
    Yik Ki Au
    Yangjian Quan
    Zuowei Xie
    Science China Chemistry, 2019, 62 : 74 - 79
  • [8] Copper catalyzed/mediated direct B–H alkenylation/alkynylation in carboranes
    Yu Chen
    Yik Ki Au
    Yangjian Quan
    Zuowei Xie
    Science China(Chemistry), 2019, 62 (01) : 74 - 79
  • [9] Copper catalyzed/mediated direct B–H alkenylation/alkynylation in carboranes
    Yu Chen
    Yik Ki Au
    Yangjian Quan
    Zuowei Xie
    Science China(Chemistry), 2019, (01) : 74 - 79
  • [10] Copper-catalyzed direct α-alkynylation of ethers under mild conditions
    Ye, Yu-Xin
    Ou, Yan-Ling
    Liang, Hao
    Zhou, Hai-Yun
    Ye, Bao-Hui
    CATALYSIS COMMUNICATIONS, 2018, 106 : 96 - 100
12345