Expedient Cobalt-Catalyzed C-H Alkynylation of (Enantiopure) Benzylamines

被引:60
|
作者
Landge, Vinod G. [1 ,3 ]
Midya, Siba P. [1 ,3 ]
Rana, Jagannath [1 ,3 ]
Shinde, Dinesh R. [2 ]
Balaraman, Ekambaram [1 ,3 ]
机构
[1] CSIR, Natl Chem Lab, Catalysis Div, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India
[2] CSIR, Natl Chem Lab, Cent NMR Facil, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India
[3] Acad Sci & Innovat Res, New Delhi 110025, India
关键词
TERMINAL ALKYNES; BOND ACTIVATION; DIRECTED FUNCTIONALIZATION; AMINOQUINOLINE BENZAMIDES; ORTHO-C(SP(2))-H BONDS; MECHANISTIC INSIGHTS; SELECTIVE ACCESS; CARBON-HYDROGEN; NICKEL; ANNULATION;
D O I
10.1021/acs.orglett.6b02549
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A unified strategy for cobalt-catalyzed ortho-C-H bond alkynylation of benzylamines is reported. Simple, commercially available CoBr2 was used as a cobalt source. The developed alkynylation strategy is robust and efficient and has a broad substrate scope including 1 degrees, 2 degrees, and 3 degrees benzylamines. The mechanistic study shows that C-H bond cleavage is reversible, and the kinetic study illustrates that the rate of reaction depends solely on the catalyst.
引用
收藏
页码:5252 / 5255
页数:4
相关论文
共 50 条
  • [41] Cobalt-Catalyzed Monoselective ortho -C-H Ethylation of Carboxamides with Triethylaluminum
    Xu, Kun
    Tan, Zhoumei
    Zhang, Haonan
    Zhang, Sheng
    SYNTHESIS-STUTTGART, 2017, 49 (17): : 3931 - 3936
  • [42] Cobalt-Catalyzed Enantioselective Directed C-H Alkylation of Indole with Styrenes
    Lee, Pin-Sheng
    Yoshikai, Naohiko
    ORGANIC LETTERS, 2015, 17 (01) : 22 - 25
  • [43] Allenes: Versatile Building Blocks in Cobalt-Catalyzed C-H Activation
    Shukla, Rahul K.
    Nair, Akshay M.
    Volla, Chandra M. R.
    SYNLETT, 2021, 32 (12) : 1169 - 1178
  • [44] Cobalt-catalyzed C-H activation and isocyanide insertion of tryptamine derivatives
    Zhu, Yiwen
    Wang, Jing
    Ying, Jun
    Wu, Xiao-Feng
    TETRAHEDRON, 2023, 143
  • [45] Cobalt-Catalyzed Annulation Reactions via C-H Bond Activation
    Prakash, Sekar
    Kuppusamy, Ramajayam
    Cheng, Chien-Hong
    CHEMCATCHEM, 2018, 10 (04) : 683 - 705
  • [46] Enantioselective electrochemical cobalt-catalyzed aryl C-H activation reactions
    von Muenchow, Tristan
    Dana, Suman
    Xu, Yang
    Yuan, Binbin
    Ackermann, Lutz
    SCIENCE, 2023, 379 (6636) : 1036 - 1042
  • [47] Electrooxidative Allene Annulations by Mild Cobalt-Catalyzed C-H Activation
    Meyer, Tjark H.
    Oliveira, Joao C. A.
    Sau, Samaresh Chandra
    Ang, Nate W. J.
    Ackermann, Lutz
    ACS CATALYSIS, 2018, 8 (10): : 9140 - 9147
  • [48] Imidate as the Intact Directing Group for the Cobalt-Catalyzed C-H Allylation
    Tanaka, Ryo
    Tanimoto, Iku
    Kojima, Masahiro
    Yoshino, Tatsuhiko
    Matsunaga, Shigeki
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20): : 13203 - 13210
  • [49] Nickel-Catalyzed C-H Alkynylation of Anilines: Expedient Access to Functionalized Indoles and Purine Nucleobases
    Ruan, Zhixiong
    Lackner, Sebastian
    Ackermann, Lutz
    ACS CATALYSIS, 2016, 6 (07): : 4690 - 4693
  • [50] Iron-Catalyzed C-H Alkynylation through Triazole Assistance: Expedient Access to Bioactive Heterocycles
    Cera, Gianpiero
    Haven, Tobias
    Ackermann, Lutz
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (15) : 3577 - 3582