Visible-light-driven electrocyclization of activated allylic amines via azomethine ylide formation

被引:38
|
作者
Yadav, Arvind K. [1 ]
Yadav, Lal Dhar S. [1 ]
机构
[1] Univ Allahabad, Dept Chem, Green Synth Lab, Allahabad 211002, Uttar Pradesh, India
关键词
Azomethine ylide; Allylic amines; Electrocyclization; Iminium ion; Photoredox catalysis; Visible light; BAYLIS-HILLMAN ADDUCTS; MERGING PHOTOREDOX CATALYSIS; C-H BONDS; EXPEDIENT SYNTHESIS; DUAL CATALYSIS; OXIDATION; PHOTOCATALYSIS; ACCESS; CONSTRUCTION; DERIVATIVES;
D O I
10.1016/j.tetlet.2014.12.063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Visible-light-driven aerobic oxidative 6 pi-electrocylization of tetrahydroisoquinoline (THIQ) derived activated allylic amines leading to functionalized tricyclic N-heterocycles is reported. The reaction proceeds through visible-light-induced formation of the iminium ion followed by azomethine ylide generation, and cyclization steps. This is the first example of visible-light-initiated catalytic electrocyclization reaction at room temperature. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:686 / 689
页数:4
相关论文
共 50 条
  • [1] Visible-Light-Driven α-Substituted Amines Enabled by In Situ Formation of Amine Substrate Aggregates
    Zhao, Yuqian
    Hou, Xiaoli
    He, Min
    Wang, Yi
    Yang, Shilei
    Wang, Wanhui
    Bao, Ming
    Yu, Xiaoqiang
    ORGANIC LETTERS, 2023, 25 (40) : 7344 - 7348
  • [2] Generation of CF3-Containing Epoxides and Aziridines by Visible-Light-Driven Trifluoromethylation of Allylic Alcohols and Amines
    Kim, Eunjin
    Choi, Sungkyu
    Kim, Heejeong
    Cho, Eun Jin
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (20) : 6209 - 6212
  • [3] Visible-Light-Driven Cyclizations
    Oueis, Emilia
    Elkadi, Mirella
    Rios, Ramon
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (04) : 635 - 697
  • [4] Visible light mediated azomethine ylide formation-photoredox catalyzed [3+2] cycloadditions
    Rueping, Magnus
    Leonori, Daniele
    Poisson, Thomas
    CHEMICAL COMMUNICATIONS, 2011, 47 (34) : 9615 - 9617
  • [5] Visible-light-driven Cadogan reaction
    Qu, Zhonghua
    Wang, Pu
    Chen, Xing
    Deng, Guo-Jun
    Huang, Huawen
    CHINESE CHEMICAL LETTERS, 2021, 32 (08) : 2582 - 2586
  • [6] Visible-Light-Driven Phosphonoalkylation of Alkenes
    Jiang, Yue-Ming
    Liu, Jie
    Fu, Qiang
    Yu, Yu-Ming
    Yu, Da-Gang
    SYNLETT, 2021, 32 (04) : 378 - 382
  • [7] Visible-light-driven Cadogan reaction
    Zhonghua Qu
    Pu Wang
    Xing Chen
    Guo-Jun Deng
    Huawen Huang
    ChineseChemicalLetters, 2021, 32 (08) : 2582 - 2586
  • [8] Selective α-oxidation of amides via visible-light-driven iron catalysis
    Liu, Shu-Hong
    Dong, Zhi-Chao
    Zang, Zhong-Lin
    Zhou, Cheng-He
    Cai, Gui-Xin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (06) : 1205 - 1212
  • [9] Visible-Light-Driven Transformations of Phenols via Energy Transfer Catalysis
    Fischer, Jerome
    Nun, Pierrick
    Coeffard, Vincent
    SYNTHESIS-STUTTGART, 2020, 52 (11): : 1617 - 1624
  • [10] Photocatalysis by Phenothiazine Dyes: Visible-Light-Driven Oxidative Coupling of Primary Amines at Ambient Temperature
    Park, Ji Hoon
    Ko, Kyoung Chul
    Kim, Eunchul
    Park, Nojin
    Ko, Ju Hong
    Ryu, Do Hyun
    Ahn, Tae Kyu
    Lee, Jin Yong
    Son, Seung Uk
    ORGANIC LETTERS, 2012, 14 (21) : 5502 - 5505