Iridium(III)- and rhodium(III)- catalyzed coupling of anilines with α-diazoesters via chelation- assisted C-H activation

被引:60
作者
Tang, Guo-Dong [1 ,2 ]
Pan, Cheng-Ling [2 ]
Li, Xingwei [2 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Anhui Univ Sci & Technol, Lab Multi Scale Mat & Mol Catalysis, Sch Mat Sci & Engn, Huainan 232001, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2016年 / 3卷 / 01期
关键词
SIMPLE INDOLE ALKALOIDS; N BOND FORMATION; DIAZO-COMPOUNDS; RH(III)-CATALYZED SYNTHESIS; DIVERGENT SYNTHESIS; ANNULATION; MILD; FUNCTIONALIZATION; BENZAMIDES; ALKYNES;
D O I
10.1039/c5qo00316d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iridium and rhodium complexes exhibited complementary activity in the coupling of N-functionalized anilines with alpha-diazoesters via C-H activation. The coupling with alpha-diazo beta-ketoesters was realized under Ir(III) catalysis to afford ester-functionalized indoles. In contrast, coupling with alpha-diazomalonates under Rh(III) catalysis afforded alkylation products without any annulation. Mechanistic studies have been performed and an iridacycle has been isolated as an intermediate.
引用
收藏
页码:87 / 90
页数:4
相关论文
共 80 条
  • [1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations
    Ackermann, Lutz
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) : 281 - 295
  • [2] Cationic Ruthenium(II) Catalysts for Oxidative C-H/N-H Bond Functionalizations of Anilines with Removable Directing Group: Synthesis of Indoles in Water
    Ackermann, Lutz
    Lygin, Alexander V.
    [J]. ORGANIC LETTERS, 2012, 14 (03) : 764 - 767
  • [3] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [4] Rhodium(III)- and Iridium(III)-Catalyzed C7 Alkylation of Indolines with Diazo Compounds
    Ai, Wen
    Yang, Xueyan
    Wu, Yunxiang
    Wang, Xuan
    Li, Yuanchao
    Yang, Yaxi
    Zhou, Bing
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) : 17653 - 17657
  • [5] Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
  • [6] Palladium@Cerium(IV) Oxide-Catalyzed Oxidative Synthesis of N-(2-Pyridyl)indoles via C-H Activation Reaction
    Chen, Jianbin
    He, Lin
    Natte, Kishore
    Neumann, Helfried
    Beller, Matthias
    Wu, Xiao-Feng
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) : 2955 - 2959
  • [7] Synthesis of N-(2-Pyridyl)indoles via Pd(II)-Catalyzed Oxidative Coupling
    Chen, Jinlei
    Pang, Qingyu
    Sun, Yanbo
    Li, Xingwei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09) : 3523 - 3526
  • [8] Rh(III)-Catalyzed Oxidative Coupling of N-Aryl-2-aminopyridine with Alkynes and Alkenes
    Chen, Jinlei
    Song, Guoyong
    Pan, Cheng-Ling
    Li, Xingwei
    [J]. ORGANIC LETTERS, 2010, 12 (23) : 5426 - 5429
  • [9] Rh(III)-catalyzed chelation-assisted intermolecular carbenoid functionalization of α-imino Csp3-H bonds
    Chen, Xun
    Xie, Ying
    Xiao, Xinsheng
    Li, Guoqiang
    Deng, Yuanfu
    Jiang, Huanfeng
    Zeng, Wei
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (83) : 15328 - 15331
  • [10] Regioselective Syntheses of 1,2-Benzothiazines by Rhodium-Catalyzed Annulation Reactions
    Cheng, Ying
    Bolm, Carsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (42) : 12349 - 12352