Rh(III)-catalyzed C-H activation/[4+3] cycloaddition of benzamides and vinylcarbenoids: facile synthesis of azepinones

被引：235
作者：
Cui, Sunliang [1 ]
Zhang, Yan
Wang, Dahai
Wu, Qifan
机构：
[1] Zhejiang Univ, Inst Mat Med, Hangzhou 310058, Zhejiang, Peoples R China
来源：
CHEMICAL SCIENCE | 2013年 / 4卷 / 10期
关键词：
N BOND FORMATION; CATALYZED OXIDATIVE CYCLOADDITION; ONE-POT SYNTHESIS; BENZOIC-ACIDS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; INTRAMOLECULAR 4+2; INTERNAL ALKYNES; RHODIUM; ANNULATION;
D O I：
10.1039/c3sc51777b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Vinylcarbenoids are used as three-carbon components in Rh(III)-catalyzed C-H activation/[4 + 3] cycloaddition with benzamides to access azepinones. This transformation makes a feature of simple starting materials, mild reaction conditions and high efficiency. A kinetic isotope effect study was conducted and a plausible mechanism is proposed.
引用
收藏
页码：3912 / 3916
页数：5
相关论文
共 50 条
  • [41] Gold-Catalyzed [4+3] Cycloaddition/C-H Functionalization Cascade: Regio- and Diastereoselective Route to Cyclohepta[b]indoles
    Li, Yangyan
    Zhu, Chao-Ze
    Zhang, Junliang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (45) : 6609 - 6613
  • [42] Rhodium(III)-catalyzed chemoselective C-H functionalization of benzamides with methyleneoxetanones controlled by the solvent
    Bian, Mengyao
    Ma, Kuangshun
    Mawjuda, Hamdulla
    Yu, Xiyong
    Li, Xingwei
    Gao, Hui
    Zhou, Zhi
    Yi, Wei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (25) : 6114 - 6118
  • [43] Isocanthine Synthesis via Rh(III)-Catalyzed Intramolecular C-H Functionalization
    Chen, Anthony Y.
    Lu, Qianqian
    Fu, Yao
    Sarpong, Richmond
    Stoltz, Brian M.
    Zhang, Haiming
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01) : 330 - 337
  • [44] Synthesis of 2-Substituted Quinolines via Rhodium(III)-Catalyzed C-H Activation of Imidamides and Coupling with Cyclopropanols
    Zhou, Xukai
    Qi, Zisong
    Yu, Songjie
    Kong, Lingheng
    Li, Yang
    Tian, Wan-Fa
    Li, Xingwei
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (10) : 1620 - 1625
  • [45] Rh(iii)-catalyzed redox-neutral C-H alkenylation of benzamides with gem-difluorohomoallylic silyl ethers via β-H elimination
    Cui, Xueli
    Qu, Jing
    Yi, Jianfeng
    Sun, Weiqiang
    Hu, Jinhui
    Guo, Suqin
    Jin, Jing-Wei
    Chen, Wen-Hua
    Wong, Wing-Leung
    Wu, Jia-Qiang
    CHEMICAL COMMUNICATIONS, 2023, 59 (25) : 3747 - 3750
  • [46] Rh(III)-Catalyzed Diastereoselective Annulation of Amides with Quinone Monoacetals: Access to Bridged Nine-Membered Heterocycles via C-H Activation
    Yang, Wei
    Dong, Jinhuan
    Wang, Jingyi
    Xu, Xianxiu
    ORGANIC LETTERS, 2017, 19 (03) : 616 - 619
  • [47] Synthesis of Functionalized Indenones via Rh-Catalyzed C-H Activation Cascade Reaction
    Lv, Ningning
    Chen, Zhengkai
    Liu, Yue
    Liu, Zhanxiang
    Zhang, Yuhong
    ORGANIC LETTERS, 2017, 19 (10) : 2588 - 2591
  • [48] Rh(III)-Catalyzed [3+2] Annulation and C-H Alkenylation of Indoles with 1,3-Diynes by C-H Activation
    Kumar, Sanjeev
    Nunewar, Saiprasad
    Usama, Khan Mohammad
    Kanchupalli, Vinaykumar
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (15) : 2223 - 2229
  • [49] Rhodium(III)-Catalyzed C-H Activation/Heterocyclization as a Macrocyclization Strategy. Synthesis of Macrocyclic Pyridones
    Krieger, Jean-Philippe
    Lesuisse, Dominique
    Ricci, Gino
    Perrin, Marc-Antoine
    Meyer, Christophe
    Cossy, Janine
    ORGANIC LETTERS, 2017, 19 (10) : 2706 - 2709
  • [50] Rh(III)-Catalyzed intramolecular redox-neutral cyclization of alkenes via C-H activation
    Shi, Zhuangzhi
    Boultadakis-Arapinis, Melissa
    Koester, Dennis C.
    Glorius, Frank
    CHEMICAL COMMUNICATIONS, 2014, 50 (20) : 2650 - 2652
12345