Vanadium-Catalyzed Dehydrogenation of N-Heterocycles in Water

被引:36
|
作者
Zumbraegel, Nadine [1 ,2 ]
Sako, Makoto [2 ]
Takizawa, Shinobu [2 ]
Sasai, Hiroaki [2 ]
Groeger, Harald [1 ]
机构
[1] Bielefeld Univ, Fac Chem, Chair Organ Chem 1, Univ Str 25, D-33615 Bielefeld, Germany
[2] Osaka Univ, ISIR, Ibaraki, Osaka 5670047, Japan
基金
日本学术振兴会;
关键词
NITROGEN-HETEROCYCLES; ACCEPTORLESS DEHYDROGENATION; REVERSIBLE DEHYDROGENATION; AEROBIC DEHYDROGENATION; QUINONE CATALYST; HYDROGENATION; NANOPARTICLES; SYSTEM; AMINES; QUINOLINES;
D O I
10.1021/acs.orglett.8b01484
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this paper, the dehydrogenation of tetrahydroquinolines using oxovanadium(V) catalysts under mild conditions in water and oxygen atmosphere is described. This catalytic technology was successfully applied to a range of other structurally related N-heterocycles, and a reaction mechanism is proposed.
引用
收藏
页码:4723 / 4727
页数:5
相关论文
共 50 条
  • [1] Gold(0) catalyzed dehydrogenation of N-heterocycles
    Kumaran, Elumalai
    Leong, Weng Kee
    TETRAHEDRON LETTERS, 2018, 59 (44) : 3958 - 3960
  • [2] Cu(I) Complexes Catalyzed the Dehydrogenation of N-Heterocycles
    Shen, Yangyang
    Chen, Fei
    Du, Zhihong
    Zhang, Hao
    Liu, Jichang
    Liu, Ning
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (07): : 4530 - 4537
  • [3] A Rare Earth Metal Catalyzed Aerobic Dehydrogenation of N-Heterocycles
    Zhang, Ting
    Lv, Yongheng
    Zhang, Zhenguo
    Jia, Zhenhua
    Loh, Teck-Peng
    ORGANIC LETTERS, 2023, 25 (24) : 4468 - 4472
  • [4] Iridium-Catalyzed Hydrogenation and Dehydrogenation of N-Heterocycles in Water under Mild Conditions
    Wang, Shengdong
    Huang, Haiyun
    Bruneau, Christian
    Fischmeister, Cedric
    CHEMSUSCHEM, 2019, 12 (11) : 2350 - 2354
  • [5] Aerobic oxidative dehydrogenation of N-heterocycles catalyzed by cobalt porphyrin
    Zhou, Weiyou
    Chen, Dongwei
    Sun, Fu'an
    Qian, Junfeng
    He, Mingyang
    Chen, Qun
    TETRAHEDRON LETTERS, 2018, 59 (10) : 949 - 953
  • [6] Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles
    Sahoo, Manoj K.
    Jaiswal, Garima
    Rana, Jagannath
    Balaraman, Ekambaram
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (57) : 14167 - 14172
  • [7] Nickel-Catalyzed Dehydrogenation of N-Heterocycles Using Molecular Oxygen
    Bera, Sourajit
    Bera, Atanu
    Banerjee, Debasis
    ORGANIC LETTERS, 2020, 22 (16) : 6458 - 6463
  • [8] Tris(pentafluorophenyl)borane-Catalyzed Acceptorless Dehydrogenation of N-Heterocycles
    Kojima, Masahiro
    Kanai, Motomu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (40) : 12224 - 12227
  • [9] On the mechanism of acceptorless dehydrogenation of N-heterocycles catalyzed by tBuOK: a computational study
    Ma, Lishuang
    Feng, Wenxu
    Zhao, Shidong
    Wang, Chuangye
    Xi, Yanyan
    Lin, Xufeng
    RSC ADVANCES, 2023, 13 (30) : 20748 - 20755
  • [10] Metal-Free Iodine-Catalyzed Oxidative Dehydrogenation of N-Heterocycles
    Li, Dengke
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (04)