Direct dehydrative cross-coupling of tautomerizable heterocycles with alkynes via Pd/Cu-catalyzed phosphonium coupling

被引:61
|
作者
Kang, Fu-An [1 ]
Lanter, James C. [1 ]
Cai, Chaozhong [1 ]
Sui, Zhihua [1 ]
Murray, William V. [1 ]
机构
[1] Johnson & Johnson Pharmaceut Res & Dev LLC, Spring House, PA 19477 USA
关键词
ARYL BOND FORMATION; C-H; DIRECT ARYLATION; ARYLBORONIC ACIDS; PROTECTING-GROUP; BORONIC ACIDS; ACTIVATION; ARENESULFONATES; ARENES;
D O I
10.1039/b917777a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first chemoselective direct dehydrative cross-coupling of tautomerizable heterocycles with alkynes has been achieved via C-H/C-OH bond activations with direct C(sp(2))-C(sp) bond formation, which is in line with ideal synthesis using readily available materials.
引用
下载
收藏
页码:1347 / 1349
页数:3
相关论文
共 50 条
  • [41] Stereoselective synthesis of (Z)-ketoeneynes via Pd(0)-Cu(I)-catalyzed cross-coupling of (Z)-ketoenol triflate with 1-alkynes
    Dai, W.-M.
    Wu, J.
    Tetrahedron, 53 (27):
  • [42] Stereoselective synthesis of (Z)-ketoeneynes via Pd(0)-Cu(I)-catalyzed cross-coupling of (Z)-ketoenol triflate with 1-alkynes
    Dai, WM
    Wu, JL
    TETRAHEDRON, 1997, 53 (27) : 9107 - 9114
  • [43] Synthesis and Functionalization of Allenes by Direct Pd-Catalyzed Organolithium Cross-Coupling
    Mateos-Gil, Jaime
    Mondal, Anirban
    Castineira Reis, Marta
    Feringa, Ben L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (20) : 7823 - 7829
  • [44] Transition-Metal (Cu, Pd, Ni)-Catalyzed Difluoroalkylation via Cross-Coupling with Difluoroalkyl Halides
    Feng, Zhang
    Xiao, Yu-Lan
    Zhang, Xingang
    ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (09) : 2264 - 2278
  • [45] Palladium-Catalyzed Oxidative Cross-Coupling between Heterocycles and Terminal Alkynes with Low Catalyst Loading
    Jie, Xiaoming
    Shang, Yaping
    Hu, Peng
    Su, Weiping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (13) : 3630 - 3633
  • [46] Copper-Catalyzed Oxidative Cross-Coupling of Sulfoximines and Alkynes
    Wang, Long
    Huang, He
    Priebbenow, Daniel L.
    Pan, Fang-Fang
    Bolm, Carsten
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (12) : 3478 - 3480
  • [47] A Pd(0)-Catalyzed Direct Dehydrative Coupling of Terminal Alkynes with Allylic Alcohols To Access 1,4-Enynes
    Li, Yang-Xiong
    Xuan, Qing-Qing
    Liu, Li
    Wang, Dong
    Chen, Yong-Jun
    Li, Chao-Jun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (34) : 12536 - 12539
  • [48] Highly regiocontrolled Pd-catalyzed cross-coupling reaction of terminal alkynes and allenylphosphine oxides
    Rubin, M
    Markov, J
    Chuprakov, S
    Wink, DJ
    Gevorgyan, V
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16): : 6251 - 6256
  • [49] Pd-Catalyzed Cross-Coupling of Terminal Alkynes with Chromium(0) Fischer Carbene Complexes
    Wang, Kang
    Wu, Fengjin
    Zhang, Yan
    Wang, Jianbo
    ORGANIC LETTERS, 2017, 19 (11) : 2861 - 2864
  • [50] Construction of Substituted Benzenes via Pd-Catalyzed Cross-Coupling/Cyclization Reaction of Vinyl Halides and Terminal Alkynes
    Xie, Meihua
    Wang, Shengke
    Wang, Jun
    Fang, Kuang
    Liu, Changqing
    Zha, Chao
    Jia, Jing
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (08): : 3329 - 3334