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
  • [21] Visible-Light-Driven Photocatalytic Activation of Inert Sulfur Ylides for 3-Acyl Oxindole Synthesis
    Xia, Xu-Dong
    Lu, Liang-Qiu
    Liu, Wen-Qiang
    Chen, Dong-Zhen
    Zheng, Yu-Han
    Wu, Li-Zhu
    Xiao, Wen-Jing
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (25) : 8432 - 8437
  • [22] A visible-light-driven transfer hydrogenation on CdS nanoparticles combined with iridium complexes
    Li, Jun
    Yang, Jinhui
    Wen, Fuyu
    Li, Can
    CHEMICAL COMMUNICATIONS, 2011, 47 (25) : 7080 - 7082
  • [23] Site-Selective Functionalization of Pyridinium Derivatives via Visible-Light-Driven Photocatalysis with Quinolinone
    Kim, Inwon
    Kang, Gyumin
    Lee, Kangjae
    Park, Bohyun
    Kang, Dahye
    Jung, Hoimin
    He, Yu-Tao
    Baik, Mu-Hyun
    Hong, Sungwoo
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (23) : 9239 - 9248
  • [24] Recent Advances in Visible-Light-Driven Photocatalyzed γ-Cyanoalkylation Reactions
    Guin, Soumitra
    Majee, Debashis
    Samanta, Sampak
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (07) : 1595 - 1618
  • [25] Visible-light-driven photocatalytic selective organic oxidation reactions
    Yang, Xue
    Zhang, Suyuan
    Li, Peixian
    Gao, Shuiying
    Cao, Rong
    JOURNAL OF MATERIALS CHEMISTRY A, 2020, 8 (40) : 20897 - 20924
  • [26] Trifluoromethylation by Visible-Light-Driven Photoredox Catalysis
    Takashi Koike
    Munetaka Akita
    Topics in Catalysis, 2014, 57 : 967 - 974
  • [27] Inactivation of algae by visible-light-driven modified photocatalysts: A review
    Yang, Yue
    Chen, Hao
    Lu, Jinfeng
    SCIENCE OF THE TOTAL ENVIRONMENT, 2023, 858
  • [28] Visible-Light-Driven α-Allylation of Carboxylic Acids
    Sun, Kai
    Ueno, Masato
    Imaeda, Keisuke
    Ueno, Kosei
    Sawamura, Masaya
    Shimizu, Yohei
    ACS CATALYSIS, 2021, 11 (15) : 9722 - 9728
  • [29] Visible-light-driven Efficient Photocatalytic Reduction of Organic Azides to Amines over CdS Sheet-rGO Nanocomposite
    Singha, Krishnadipti
    Mondal, Aniruddha
    Ghosh, Subhash Chandra
    Panda, Asit Baran
    CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (03) : 255 - 260
  • [30] Trifluoromethylation by Visible-Light-Driven Photoredox Catalysis
    Koike, Takashi
    Akita, Munetaka
    TOPICS IN CATALYSIS, 2014, 57 (10-13) : 967 - 974