Copper-Catalyzed C(sp2)-H Amidation with Azides as Amino Sources

被引:110
作者
Peng, Jiangling [1 ]
Xie, Zeqiang [1 ]
Chen, Ming [1 ]
Wang, Jian [1 ]
Zhu, Qiang [1 ]
机构
[1] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, State Key Lab Resp Dis, Guangzhou 510530, Guangdong, Peoples R China
基金
美国国家科学基金会;
关键词
C-H AMIDATION; N BOND FORMATION; DIRECT AMINATION; ORGANIC AZIDES; OXIDATIVE FUNCTIONALIZATION; INTERMOLECULAR AMIDATION; ACYL AZIDES; ARENES; ACTIVATION; CARBAZOLES;
D O I
10.1021/ol502010g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed C-H amidation process, with azides as amino sources under oxidant-free conditions, has been developed. When N-heterocycles were employed as directing groups, sulfonylazide and benzoylazide could be used as amidating reagents to provide corresponding N-arylamides. When amidines or imine were used, tandem C-N/N-N bond formation occurred to afford indazole derivatives in one pot.
引用
收藏
页码:4702 / 4705
页数:4
相关论文
共 50 条
  • [31] Copper-catalyzed asymmetric C(sp2)-H arylation for the synthesis of P- and axially chiral phosphorus compounds
    Yan, Shao-Bai
    Wang, Rui
    Li, Zha-Gen
    Li, An-Na
    Wang, Chuanyong
    Duan, Wei-Liang
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [32] Copper-Catalyzed Functionalization of Aza-Aromatic Rings with Fluoroalcohols via Direct C(sp2)-H/C(sp3)-H Coupling Reactions
    Chen, Jie
    Li, Meng
    Zhang, Jinli
    Sun, Wangbin
    Jiang, Yaojia
    ORGANIC LETTERS, 2020, 22 (08) : 3033 - 3038
  • [33] Copper-Catalyzed One-Pot Synthesis of Imidazo/Benzoimidazoquinazolinones by Sequential Ullmann-Type Coupling and Intramolecular C-H Amidation
    Xu, Hao
    Fu, Hua
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (04) : 1180 - 1186
  • [34] Enantioselective Synthesis of Axially Chiral Tetrasubstituted Alkenes by Copper-Catalyzed C(sp2)-H Functionalization of Arenes with Vinyl Cations
    Weng, Chen-Yong
    Liu, Li-Gao
    Sun, Miao
    Lu, Xin
    Hong, Xin
    Ye, Long-Wu
    Zhou, Bo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (06)
  • [35] Copper-catalyzed C(sp)-C(sp2) oxidative cross coupling reaction to access to methyl arylpropiolates at room temperature
    Min, Jinghong
    Zheng, Zhanjiang
    Huang, Shuaishuai
    He, Rongrong
    Xu, Zheng
    Bouillon, Jean Philippe
    Xu, Liwen
    GREEN SYNTHESIS AND CATALYSIS, 2021, 2 (04): : 350 - 355
  • [36] Copper-Catalyzed C(sp3)-H Amidation: Sterically Driven Primary and Secondary C-H Site-Selectivity
    Bakhoda, Abolghasem
    Jiang, Quan
    Badiei, Yosra M.
    Bertke, Jeffery A.
    Cundari, Thomas R.
    Warren, Timothy H.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (11) : 3421 - 3425
  • [37] One-Pot Synthesis of Triazoloquinazolinones via Copper-Catalyzed Tandem Click and Intramolecular C-H Amidation
    Selvaraju, Manikandan
    Sun, Chung-Ming
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (06) : 1329 - 1336
  • [38] Cobalt-Catalyzed Ortho-C(sp2)-H Amidation of Benzaldehydes with Dioxazolones Using Transient Directing Groups
    Huang, Jie
    Ding, Jun
    Ding, Tong-Mei
    Zhang, Shuiyi
    Wang, Yaqiu
    Sha, Feng
    Zhang, Shu-Yu
    Wu, Xin-Yan
    Li, Qiong
    ORGANIC LETTERS, 2019, 21 (18) : 7342 - 7345
  • [39] Copper-Catalyzed Intramolecular Oxidative C(sp3)- H Amidation of 2-Aminoacetophenones: Efficient Synthesis of Indoline-2,3-diones
    Huang, Jinbo
    Mao, Tingting
    Zhu, Qiang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (14) : 2878 - 2882
  • [40] Room Temperature Benzofused Lactam Synthesis Enabled by Cobalt(III)-Catalyzed C(sp2)-H Amidation
    Tian, Xun
    Li, Xin
    Duan, Shengzu
    Du, Ya
    Liu, Tongqi
    Fang, Yongsheng
    Chen, Wen
    Zhang, Hongbin
    Li, Minyan
    Yang, Xiaodong
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (04) : 1050 - 1058