Electrochemically Driven Ugi-Azide Reaction via C(sp3)-H Bond Activation of Tertiary Amines

被引：0
作者：
Song, Bin [1 ]
Zhao, Feng [1 ]
Gao, Pengxiang [1 ]
Wang, Ruizong [1 ]
Ju, Xuehai [1 ]
Hu, Bingcheng [1 ]
Zhang, Chong [1 ]
机构：
[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Jiangsu, Peoples R China
来源：
ORGANIC LETTERS | 2025年 / 27卷 / 06期
基金：
中国国家自然科学基金;
关键词：
TETRAZOLES; FUNCTIONALIZATION; ISOCYANIDES; AMMONIA;
D O I：
10.1021/acs.orglett.5c00163
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An electrochemically driven Ugi-azide reaction was established via C(sp3)-H bond activation of tertiary amines to prepare alpha-aminomethyl tetrazoles within 2.5 h under mild conditions with remarkable tolerance of various functional groups. Besides, this electrochemical strategy not only obviated the needs of iodine, metal, and exogenous oxidant but possessed potential applicability of convenient large-scale synthesis. Mechanistic studies indicated both the alkyl carbon-centered radical generated at the anode and intramolecular [3 + 2] cycloaddition are key factors for this strategy.
引用
收藏
页码：1561 / 1567
页数：7
相关论文
共 49 条
  • [1] Electrochemically-driven difunctionalization of the isocyanide and Mumm rearrangement cascade: expeditious synthesis of N-acyl-N-alkyl S-thiocarbamates
    Bhati, Kuldeep Singh
    Sharma, Siddharth
    [J]. CHEMICAL COMMUNICATIONS, 2024, 60 (57) : 7355 - 7358
  • [2] Recent Applications of Homogeneous Catalysis in Electrochemical Organic Synthesis
    Cheng, Xu
    Lei, Aiwen
    Mei, Tian-Sheng
    Xu, Hai-Chao
    Xu, Kun
    Zeng, Chengchu
    [J]. CCS CHEMISTRY, 2022, 4 (04): : 1120 - 1152
  • [3] Iron-Catalysed Oxidative Ugi-Type Multicomponent Reaction Using (Arylmethyl)amines as Imine Precursors
    Dighe, Shashikant U.
    Kolle, Shivalinga
    Batra, Sanjay
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (19) : 4238 - 4245
  • [4] 1-isocyanomethylbenzotriazole and 2,2,4,4-tetramethylbutylisocyanide -: cleavable isocyanides useful-for the preparation of α-aminomethyl tetrazoles
    Dömling, Alexander
    Beck, Barbara
    Magnin-Lachaux, Marina
    [J]. TETRAHEDRON LETTERS, 2006, 47 (25) : 4289 - 4291
  • [5] Electrochemical generation and utilization of alkoxy radicals
    El Gehani, Albara A. M. A.
    Maashi, Hussain A.
    Harnedy, James
    Morrill, Louis C.
    [J]. CHEMICAL COMMUNICATIONS, 2023, 59 (25) : 3655 - 3664
  • [6] Two-Step Route to Diverse N-Functionalized Peptidomimetic-like Isatins through an Oxidation/Intramolecular Oxidative-Amidation Cascade of Ugi Azide and Ugi Three-Component Reaction Products
    Foley, Christopher
    Shaw, Arthur
    Hulme, Christopher
    [J]. ORGANIC LETTERS, 2016, 18 (19) : 4904 - 4907
  • [7] Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones
    Fu, Niankai
    Li, Longji
    Yang, Qi
    Luo, Sanzhong
    [J]. ORGANIC LETTERS, 2017, 19 (08) : 2122 - 2125
  • [8] Electrochemical strategies for N-cyanation of secondary amines and α C-cyanation of tertiary amines under transition metal-free conditions
    Fu, Zhengjiang
    Fu, Yaping
    Yin, Jian
    Hao, Guangguo
    Yi, Xuezheng
    Zhong, Tingting
    Guo, Shengmei
    Cai, Hu
    [J]. GREEN CHEMISTRY, 2021, 23 (23) : 9422 - 9427
  • [9] C-H functionalization enabled by multiple isocyanides
    Gao, Mingchun
    Lu, Shaohang
    Xu, Bin
    [J]. CHEMICAL SOCIETY REVIEWS, 2024, 53 (20) : 10147 - 10170
  • [10] Recent Advances in the Electrochemical Functionalization of Isocyanides
    Gu, Qingyun
    Cheng, Zhenfeng
    Qiu, Xiaodong
    Zeng, Xiaobao
    [J]. CHEMICAL RECORD, 2023, 23 (01)
12345