Electrochemical synthesis of α-amino amides via C(sp3)-H bond activation

被引:14
|
作者
Guan, Zhipeng [1 ]
Peng, Yanan [1 ]
Yang, Dongfeng [1 ]
Zhu, Shuxiang [1 ]
Zhang, Heng [1 ]
Lei, Aiwen [1 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies IAS, Wuhan 430072, Hubei, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金; 国家重点研发计划;
关键词
MULTICOMPONENT REACTIONS; FUNCTIONALIZATION; ELECTROSYNTHESIS; DERIVATIVES; ALKYNES;
D O I
10.1039/d2gc00530a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Multicomponent reactions provide a fast and efficient tool to construct various high-value molecules in the field of synthetic chemistry. Herein, we report a novel electrochemical oxidative four-component reaction for the synthesis of alpha-amino amides via C(sp(3))-H bond activation. The active intermediate generated by the difunctionalization of isocyanide undergoes intermolecular rearrangement rather than the easier intramolecular rearrangement. This may be caused by a six-member ring transition state. In addition, under metal-free and external oxidant-free conditions, large-scale synthesis and good functional group tolerance indicated the potential applicability of this methodology.
引用
收藏
页码:3964 / 3968
页数:5
相关论文
共 50 条
  • [21] Recent Advances in the Synthesis of Heterocyclic Compounds via Pd-Catalyzed C(sp3)-H Bond Activation
    Zhao, Kang
    Yang, Lei
    Liu, Jianhua
    Xia, Chungu
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (11) : 2833 - 2857
  • [22] γ-C (sp3)-H bond functionalisation of α,β-unsaturated amides through an umpolung strategy
    Futaki, Erika
    Takeda, Norihiko
    Yasui, Motohiro
    Shinada, Tetsuro
    Miyata, Okiko
    Ueda, Masafumi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (08) : 1563 - 1566
  • [23] Enantioselective Formal C(sp3)-H Bond Activation in the Synthesis of Bioactive Spiropyrazolone Derivatives
    Li, Houhua
    Gontla, Rajesh
    Flegel, Jana
    Merten, Christian
    Ziegler, Slava
    Antonchick, Andrey P.
    Waldmann, Herbert
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (01) : 307 - 311
  • [24] C(sp3)-C(sp3) Bond Formation via Electrochemical Alkoxylation and Subsequent Lewis Acid Promoted Reactions
    Lopez, Enol
    van Melis, Carlo
    Martin, Raul
    Petti, Alessia
    de la Hoz, Antonio
    Diaz-Ortiz, Angel
    Dobbs, Adrian P.
    Lam, Kevin
    Alcazar, Jesus
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (19) : 4521 - 4525
  • [25] Palladium-catalyzed unactivated β-methylene C(sp3)-H bond alkenylation of aliphatic amides and its application in a sequential C(sp3)-H/C(sp2)-H bond alkenylation
    Shan, Gang
    Huang, Guiyi
    Rao, Yu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (03) : 697 - 701
  • [26] C(sp3)-F, C(sp2)-F and C(sp3)-H bond activation at silicon(II) centers
    Swamy, V. S. V. S. N.
    Parvin, Nasrina
    Raj, K. Vipin
    Vanka, Kumar
    Sen, Sakya S.
    CHEMICAL COMMUNICATIONS, 2017, 53 (71) : 9850 - 9853
  • [27] Electrochemical Intramolecular Oxidative C(sp3)-H/C(sp3)-H Coupling for the Synthesis of 4-Quinolones
    Wu, Jiwei
    Jin, Kejun
    Wang, Ruiyou
    Wang, Xingyu
    Yu, Xiaoxiao
    Zhong, Liangcheng
    Liu, Jianguo
    SYNTHESIS-STUTTGART, 2023, 55 (03): : 451 - 456
  • [28] Activation of O2 across a C(sp3)-C(sp3) bond
    Kumar, Rahul
    Richter, Stefan
    Maity, Suvendu
    Sarkar, Pallavi
    Chrysochos, Nicolas
    Pati, Swapan K.
    Ghosh, Prasanta
    Schulzke, Carola
    Jana, Anukul
    CHEMICAL COMMUNICATIONS, 2022, 58 (19) : 3122 - 3125
  • [29] Oxidative Alkylarylation of N-Aryl Bicyclobutyl Amides with C(sp3)-H Feedstocks via C(sp3)-H/C(sp2)-H Functionalization
    Yuan, Jing
    Zhou, Jiao
    Xia, Peng-Fei
    Liu, Yu
    Tang, Ke-Wen
    Fan, Jian-Hong
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (24) : 3399 - 3404
  • [30] Catalytic alkylation of unactivated C(sp3)-H bonds for C(sp3)-C(sp3) bond formation
    Chen, Zhen
    Rong, Meng-Yu
    Nie, Jing
    Zhu, Xue-Feng
    Shi, Bing-Feng
    Ma, Jun-An
    CHEMICAL SOCIETY REVIEWS, 2019, 48 (18) : 4921 - 4942