Co(iii)-catalyzed Z-selective oxidative C-H/C-H cross-coupling of alkenes with triisopropylsilylacetylene

被引:18
|
作者
Zhao, Tingxing [1 ]
Qin, Dekun [1 ]
Han, Weiguo [1 ]
Yang, Shiping [1 ]
Feng, Boya [1 ]
Gao, Ge [1 ]
You, Jingsong [1 ]
机构
[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, 29 Wangjiang Rd, Chengdu 610064, Sichuan, Peoples R China
关键词
TERMINAL ALKYNES; CARBONYL-COMPOUNDS; O-ANNULATION; ALKYNYLATION; ACCESS; AMIDES; BONDS; ENYNES; BENZANNULATION; COMPLEXES;
D O I
10.1039/c9cc02347j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Co(III)-catalyzed direct oxidative C-H/C-H cross-coupling reaction of acrylamides with triisopropylsilylacetylene is presented. It is applicable to unsubstituted, internal and terminal acrylamides with a broad functionality tolerance. The feasibility of this protocol is successfully demonstrated by the late-stage alkynylation of a derivative of steroid drug Epristeride.
引用
收藏
页码:6118 / 6121
页数:4
相关论文
共 50 条
  • [21] Iron-Catalyzed Oxidative C-H/C-H Cross-Coupling: An Efficient Route to α-Quaternary α-Amino Acid Derivatives
    Li, Kaizhi
    Tan, Guangying
    Huang, Jingsheng
    Song, Feijie
    You, Jingsong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (49) : 12942 - 12945
  • [22] Rhodium catalysed cross-coupling of alkenes by C-H activation: Addition of alkenic C-H bonds of 2-vinylpyridines to alkenes
    Lim, YG
    Kang, JB
    Kim, YH
    CHEMICAL COMMUNICATIONS, 1996, (05) : 585 - 586
  • [23] Cobalt-Catalyzed Oxidative C-H/N-H Cross-Coupling: Selective and Facile Access to Triarylamines
    Du, Cong
    Li, Peng-Xiang
    Zhu, Xinju
    Han, Jiao-Na
    Niu, Jun-Long
    Song, Mao-Ping
    ACS CATALYSIS, 2017, 7 (04): : 2810 - 2814
  • [24] PdII-Catalyzed Regio- and Enantioselective Oxidative C-H/C-H Cross-Coupling Reaction between Ferrocenes and Azoles
    Cai, Zhong-Jian
    Liu, Chen-Xu
    Gu, Qing
    Zheng, Chao
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (07) : 2149 - 2153
  • [25] Pd(II)-Catalyzed Azine-Assisted Enantioselective Oxidative C-H/C-H Cross-Coupling of Ferrocenes with Various Heteroarenes
    Cao, Feifei
    Chen, Qian
    Shan, He
    Ling, Li
    Hu, Jianfeng
    Zhang, Hao
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (01): : 479 - 487
  • [26] Stoichiometric copper or silver salt-mediated oxidative C-H/C-H cross-coupling reactions
    Dong, Jiaxing
    Wu, Qian
    You, Jingsong
    TETRAHEDRON LETTERS, 2015, 56 (13) : 1591 - 1599
  • [27] Tandem oxidation-oxidative C-H/C-H cross-coupling: synthesis of arylquinones from hydroquinones
    Zhang, Shuai
    Song, Feijie
    Zhao, Dongbing
    You, Jingsong
    CHEMICAL COMMUNICATIONS, 2013, 49 (40) : 4558 - 4560
  • [28] Palladium-Catalyzed Direct Oxidative C-H Cross-Coupling of Azoarenes with Alcohols
    Tang, Hui
    Qian, Cheng
    Lin, Dongen
    Jiang, Huanfeng
    Zeng, Wei
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (2-3) : 519 - 527
  • [29] Palladium-catalyzed oxidative direct C-H/C-H cross coupling of anilides with β-keto esters
    Chan, Wai-Wing
    Zhou, Zhongyuan
    Yu, Wing-Yiu
    CHEMICAL COMMUNICATIONS, 2013, 49 (74) : 8214 - 8216
  • [30] Coupling of Nitrogen Heteroaromatics and Alkanes without Transition Metals: A New Oxidative Cross-Coupling at C-H/C-H Bonds
    Deng, Guojun
    Ueda, Kirika
    Yanagisawa, Shuichi
    Itami, Kenichiro
    Li, Chao-Jun
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (02) : 333 - 337