A Facile Electrochemical Strategy for the Azidation of Benzylic C(sp3)-H Bonds

被引:8
作者
He, Guoxue [1 ,2 ]
Li, Yutian [1 ,2 ]
Zhou, Shengbin [1 ,2 ]
Yang, Xiaohao [1 ,2 ]
Shang, Aolong [1 ,2 ]
Wang, Yunbo [1 ,2 ]
Liu, Hong [1 ,2 ,3 ]
Zhou, Yu [1 ,2 ,3 ]
机构
[1] UCAS, Hangzhou Inst Adv Study, Sch Pharmaceut Sci & Technol, Hangzhou 310024, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
基金
中国国家自然科学基金;
关键词
Azidation; Benzyl; C-N bonds; C(sp(3))-H; Electrochemistry; METAL-CATALYZED AZIDATION; C-H BONDS; CLICK CHEMISTRY; COUPLING REACTIONS; AMINATION; AZOLES; FUNCTIONALIZATION; CYCLOADDITION; SUBSTITUTION; DIVERSITY;
D O I
10.1002/ejoc.202201041
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report a direct azidation of benzylic C(sp(3))-H bonds via an electrochemical process, which use cheap and durable graphite plates as electrodes, without any external oxidants or metal catalysts. This protocol is a novel, green and environmentally benign synthetic strategy to achieve azidation of C(sp(3))-H in benzylic group. More importantly, these azidation products are suitable for late-stage functionalization to afford diversified triazole and tetrazole derivatives.
引用
收藏
页数:4
相关论文
共 65 条
  • [1] Click Chemistry: 1,2,3-Triazoles as Pharmacophores
    Agalave, Sandip G.
    Maujan, Suleman R.
    Pore, Vandana S.
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) : 2696 - 2718
  • [2] [Anonymous], 2011, ANGEW CHEM
  • [3] [Anonymous], 2011, ANGEW CHEM, V123, P11689
  • [4] [Anonymous], 2013, ANGEW CHEM
  • [5] Electrochemical Benzylic C(sp3)-H Acyloxylation
    Atkins, Alexander P.
    Rowett, Albert C.
    Heard, David M.
    Tate, Joseph A.
    Lennox, Alastair J. J.
    [J]. ORGANIC LETTERS, 2022, : 5105 - 5108
  • [6] C-N bond forming cross-coupling reactions: an overview
    Bariwal, Jitender
    Van der Eycken, Erik
    [J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) : 9283 - 9303
  • [7] Ruthenium-catalyzed azide-alkyne cycloaddition: Scope and mechanism
    Boren, Brant C.
    Narayan, Sridhar
    Rasmussen, Lars K.
    Zhang, Li
    Zhao, Haitao
    Lin, Zhenyang
    Jia, Guochen
    Fokin, Valery V.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) : 8923 - 8930
  • [8] Bosnidou A.E., 2019, Angew. Chem, V131, P7564
  • [9] Intermolecular Radical C(sp3)-H Amination under Iodine Catalysis
    Bosnidou, Alexandra E.
    Muniz, Kilian
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (22) : 7485 - 7489
  • [10] Organic azides:: An exploding diversity of a unique class of compounds
    Bräse, S
    Gil, C
    Knepper, K
    Zimmermann, V
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) : 5188 - 5240