Regiodivergent C-H Annulation of Imines with Unsymmetrical Alkynes Using Transient Directing Alcohols via Rh(III) Catalysis

被引:6
作者
Liu, Bairong [1 ]
Chen, Yabo [1 ]
Liang, Qixin [1 ]
Liang, Yuyao [1 ]
Liu, Bifu [2 ]
Liu, Yuan [1 ]
Gao, Yang [1 ]
Chen, Qian [1 ]
Huo, Yanping [1 ]
Li, Xianwei [1 ]
机构
[1] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Peoples R China
[2] Huizhou Univ, Sch Chem & Mat Engn, Huizhou 516007, Peoples R China
基金
美国国家科学基金会;
关键词
regioselectivity; unsymmetrical alkynes; transformable directing groups; dual and triple C-H annulation; fused rings; N BOND FORMATION; AROMATIC KETIMINES; PROPARGYL ALCOHOLS; ORTHO-ALKENYLATION; INTERNAL ALKYNES; ACTIVATION; FUNCTIONALIZATION; HYDROARYLATION; CYCLOADDITION; BENZAMIDES;
D O I
10.1002/adsc.202300167
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Regiodivergent [3+2] and [4+2] C-H annulation of imines and imidate esters with unsymmetrical alkynes has been achieved under Rh(III) catalysis. Further transformation of the aldehyde and TMS functionality on the indene products is also demonstrated. The current work highlights the alcohols-directed multiple C-H annulation of imines and imidate esters, leading to diverse fused heterocycles.
引用
收藏
页码:2018 / 2025
页数:8
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共 91 条
  • [11] Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N-O Bond as a Handle for C-N Bond Formation and Catalyst Turnover
    Guimond, Nicolas
    Gouliaras, Christina
    Fagnou, Keith
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (20) : 6908 - +
  • [12] Isoquinoline Synthesis via Rhodium-Catalyzed Oxidative Cross-Coupling/Cyclization of Aryl Aldimines and Alkynes
    Guimond, Nicolas
    Fagnou, Keith
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) : 12050 - +
  • [13] Metal-Catalyzed Annulations through Activation and Cleavage of C-H Bonds
    Gulias, Moises
    Luis Mascarenas, Jose
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) : 11000 - 11019
  • [14] Development of transition-metal-catalyzed cycloaddition reactions leading to polycarbocyclic systems
    Gulias, Moises
    Lopez, Fernando
    Mascarenas, Jose L.
    [J]. PURE AND APPLIED CHEMISTRY, 2011, 83 (03) : 495 - 506
  • [15] Ruthenium(II)-Catalyzed Regio- and Stereoselective Hydroarylation of Alkynes via Directed C-H Functionalization
    Hashimoto, Yuto
    Hirano, Koji
    Satoh, Tetsuya
    Kakiuchi, Fumitoshi
    Miura, Masahiro
    [J]. ORGANIC LETTERS, 2012, 14 (08) : 2058 - 2061
  • [16] Rh(III)-Catalyzed bilateral cyclization of aldehydes with nitrosos toward unsymmetrical acridines proceeding with C-H functionalization enabled by a transient directing group
    Hu, Weiming
    Zheng, Qingheng
    Sun, Song
    Cheng, Jiang
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (46) : 6263 - 6266
  • [17] Regioselective C-H Hydroarylation of Internal Alkynes with Arenecarboxylates: Carboxylates as Deciduous Directing Groups
    Huang, Liangbin
    Biafora, Agostino
    Zhang, Guodong
    Bragoni, Valentina
    Goossen, Lukas J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (24) : 6933 - 6937
  • [18] Rhodium-Catalyzed Synthesis of Isoquinolines and Indenes from Benzylidenehydrazones and Internal Alkynes
    Huang, Xiao-Cheng
    Yang, Xu-Heng
    Song, Ren-Jie
    Li, Jin-Heng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03) : 1025 - 1031
  • [19] The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3-Aliphatic-Substituted Indoles and Pyrroles
    Huestis, Malcolm P.
    Chan, Lina
    Stuart, David R.
    Fagnou, Keith
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (06) : 1338 - 1341
  • [20] Rhodium-Catalyzed Oxidative Cycloaddition of Benzamides and Alkynes via C-H/N-H Activation
    Hyster, Todd K.
    Rovis, Tomislav
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (30) : 10565 - 10569