γ-Amino Butyric Acid (GABA) Synthesis Enabled by Copper-Catalyzed Carboamination of Alkenes

被引:57
|
作者
Zhu, Nengbo [1 ]
Wang, Ting [2 ]
Ge, Liang [1 ]
Li, Yajun [1 ]
Zhang, Xinhao [2 ]
Bao, Hongli [1 ]
机构
[1] Univ Chinese Acad Sci, State Key Lab Struct Chem, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, 155 Yangqiao Rd West, Fuzhou 350002, Fujian, Peoples R China
[2] Peking Univ, Shenzhen Grad Sch, Key Lab Chem Genom, Lab Computat Chem & Drug Design, Shenzhen 518055, Peoples R China
关键词
POLAR CROSSOVER REACTIONS; BOND-FORMING REACTIONS; FREE-RADICAL REACTIONS; C-H ACTIVATION; ALKYL NITRILES; ACETONITRILE; FUNCTIONALIZATION; PYRROLIDINE; MECHANISM; CASCADE;
D O I
10.1021/acs.orglett.7b01969
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
gamma-Amino butyric acid" (GABA) is the chief inhibitory neurotransmitter in the mammalian central nervous system. Many GABA derivatives are used clinically to prevent or treat neurodegenerative diseases. Copper-catalyzed carboamination of alkenes offers an efficient method to fashion the core structure of GABA derivatives from alkenes. In this reaction, acetonitrile serves as the source of the carbon and nitrogen functionalities used to difunctionalize alkenes. Experimental and density functional theory (DFT) studies were carried out to investigate the mechanism of the reaction, and a copper-catalyzed radical polar crossover mechanism is proposed.
引用
收藏
页码:4718 / 4721
页数:4
相关论文
共 50 条
  • [41] Synthesis of Difluoromethylated Alkenes via Copper-Catalyzed Protodefluorination of ß-(Trifluoromethyl)styrenes
    Dong, Tao
    Ye, Yibin
    Wang, Yanhui
    Cheung, Kelvin Pak Shing
    Tsui, Gavin Chit
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (19)
  • [42] Copper-Catalyzed Oxidative Trifluoromethylation of Aromatic Alkenes for the Synthesis of α-Trifluoromethylated Ketones
    Wang, Jiali
    Liu, Hongjian
    Qi, Chaorong
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (03)
  • [43] Stereoselective synthesis of vinylsilanes via copper-catalyzed silylation of alkenes with silanes
    Gu, Jian
    Cai, Chun
    CHEMICAL COMMUNICATIONS, 2016, 52 (71) : 10779 - 10782
  • [44] Copper-Catalyzed Carbonylative Synthesis of β-Boryl Amides via Boroamidation of Alkenes
    Wu, Fu-Peng
    Holz, Jens
    Yuan, Yang
    Wu, Xiao-Feng
    CCS CHEMISTRY, 2021, 3 (04): : 2643 - 2654
  • [45] Ligand-Enabled, Copper-Catalyzed Electrophilic Amination for the Asymmetric Synthesis of beta-Amino Acids
    Tak, Raj K.
    Noda, Hidetoshi
    Shibasaki, Masakatsu
    ORGANIC LETTERS, 2021, 23 (21) : 8617 - 8621
  • [46] Insight into the Copper-Catalyzed Borylation of Strained Alkenes
    Parra, Alejandro
    Lopez, Aurora
    Diaz-Tendero, Sergio
    Amenos, Laura
    Garcia Ruano, Jose Luis
    Tortosa, Mariola
    SYNLETT, 2015, 26 (04) : 494 - 500
  • [47] Copper-Catalyzed Bromodifluoroacetylation of Alkenes with Ethyl Bromodifluoroacetate
    Li, Dengke
    Mao, Tingting
    Huang, Jinbo
    Zhu, Qiang
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (17): : 10445 - 10452
  • [48] Copper-Catalyzed Vicinal Thiocyanosulfonylation of Alkenes and Alkynes
    Duan, Meng-Fan
    Xiao, Mei
    Ogundipe, Olukayode Olamiji
    Wu, Xin-Xin
    Zou, Jian-Ping
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (16): : 11558 - 11566
  • [49] Enantioselective Copper-Catalyzed Carboetherification of Unactivated Alkenes
    Bovino, Michael T.
    Liwosz, Timothy W.
    Kendel, Nicole E.
    Miller, Yan
    Tyminska, Nina
    Zurek, Eva
    Chemler, Sherry R.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (25) : 6383 - 6387
  • [50] Copper-Catalyzed Enantioselective Radical Chlorination of Alkenes
    Wu, Dunqi
    Fan, Wenzheng
    Wu, Lianqian
    Chen, Pinhong
    Liu, Guosheng
    ACS CATALYSIS, 2022, 12 (09) : 5284 - 5291