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
  • [1] Rhodium-Catalyzed C(sp2)-H Amidation of Azine with Sulfonamides
    Vu, Huu-Manh
    Yong, Jia-Yuan
    Chen, Fei-Wu
    Li, Xu-Qin
    Shi, Guo-Qing
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (07) : 4963 - 4972
  • [2] Copper-Catalyzed Intramolecular C(sp3)-H and C(sp2)-H Amidation by Oxidative Cyclization
    Wang, Zhen
    Ni, Jizhi
    Kuninobu, Yoichiro
    Kanai, Motomu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (13) : 3496 - 3499
  • [3] Ruthenium-Catalyzed Ortho C(sp2)-H Amidation of Benzaldehydes with Organic Azides
    Rasheed, Omer K.
    SYNLETT, 2018, 29 (08) : 1033 - 1036
  • [4] Iridium-Catalyzed ortho-C(sp2)-H Amidation of Benzaldehydes with Organic Azides
    Mu, Delong
    Wang, Xinmou
    Chen, Gong
    He, Gang
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (08) : 4497 - 4503
  • [5] para-Selective copper-catalyzed C(sp2)-H amidation/dimerization of anilides via a radical pathway
    Viveki, Amol B.
    Garad, Dnyaneshwar N.
    Gonnade, Rajesh G.
    Mhaske, Santosh B.
    CHEMICAL COMMUNICATIONS, 2020, 56 (10) : 1565 - 1568
  • [6] Copper-Catalyzed Direct Acyloxylation of C(sp2)-H Bonds in Aromatic Amides
    Wang, Feifan
    Hu, Qiyan
    Shu, Chao
    Lin, Zhiyang
    Min, Dewen
    Shi, Tianchao
    Zhang, Wu
    ORGANIC LETTERS, 2017, 19 (13) : 3636 - 3639
  • [7] Chelation-Assisted Rhodium-Catalyzed Direct Amidation with Amidobenziodoxolones: C(sp2)-H, C(sp3)-H, and Late-Stage Functionalizations
    Hu, Xu-Hong
    Yang, Xiao-Fei
    Loh, Teck-Peng
    ACS CATALYSIS, 2016, 6 (09): : 5930 - 5934
  • [8] Stereoretentive Copper-Catalyzed Directed Thioglycosylation of C(sp2)-H Bonds of Benzamides
    Chabrier, Amelie
    Bruneau, Alexandre
    Benmahdjoub, Sara
    Benmerad, Belkacem
    Belaid, Sabrina
    Brion, Jean-Daniel
    Alami, Mouad
    Messaoudi, Samir
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (42) : 15006 - 15010
  • [9] Copper-catalyzed direct acyloxylation of C(sp2)-H bonds with Benzoic acids
    Zhao, Sheng
    Chen, Fa-Jie
    Liu, Bin
    Shi, Bing-Feng
    SCIENCE CHINA-CHEMISTRY, 2015, 58 (08) : 1302 - 1309
  • [10] Ru(II)-catalyzed amidation reactions of 8-methylquinolines with azides via C(sp3)-H activation
    Liu, Bingxian
    Li, Bin
    Wang, Baiquan
    CHEMICAL COMMUNICATIONS, 2015, 51 (91) : 16334 - 16337