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] Conjugated polymers for visible-light-driven photocatalysis
    Dai, Chunhui
    Liu, Bin
    ENERGY & ENVIRONMENTAL SCIENCE, 2020, 13 (01) : 24 - 52
  • [22] 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
  • [23] Visible-light-driven organic transformations on semiconductors
    Han, Guanqun
    Sun, Yujie
    MATERIALS TODAY PHYSICS, 2021, 16
  • [24] Visible-light-driven C(sp3)-H alkylation of heterobenzylic amines via electron donor-acceptor complexes
    Huo, Yumei
    Chen, Beibei
    Xu, Zhaoqing
    Ren, Xiaoyu
    Qi, Rupeng
    Wang, Chao
    ORGANIC CHEMISTRY FRONTIERS, 2023, 11 (01) : 205 - 210
  • [25] Copper Phenylacetylide and TiO2 Modification for an Efficient Visible-Light-Driven Oxidative Coupling of Amines
    Yu, Chunzheng
    Zhou, Yiwei
    Zhou, Ye
    Liu, Zhenkun
    Liang, Mao
    Huang, Lei
    Zhao, Jian
    ACS APPLIED MATERIALS & INTERFACES, 2024, 16 (18) : 23178 - 23188
  • [26] Visible-light-driven selective alcohol dehydrogenation and hydrogenolysis via the Mott Schottky effect
    Yang, Xue
    Zhang, Suyuan
    Tao, Huilin
    Yan, Xuyan
    Tan, Yanxi
    Zhang, Yongfan
    Gao, Shuiying
    Cao, Rong
    JOURNAL OF MATERIALS CHEMISTRY A, 2020, 8 (14) : 6854 - 6862
  • [27] Visible-light-driven hydrogen evolution from waste toner powder activated by Ni species
    Zhang, Wenyan
    Guan, Hangmin
    Hu, Yingfei
    Wang, Wei
    Hao, Linyun
    Yang, Xiaoli
    Tian, Wenjie
    GREEN CHEMISTRY, 2022, 24 (03) : 1335 - 1341
  • [28] Visible-Light-Driven Heterocyclic Fluoroalkylation Via Electron Donor-Acceptor Complexes
    Li, Yufei
    Xie, Kaili
    Yang, Shimin
    Dai, Peng
    Guo, Jianbo
    Gu, Yucheng
    Xia, Qing
    Zhang, Weihua
    CHEMCATCHEM, 2024, 16 (20)
  • [29] Visible-light-driven synthesis of indoles via aerobic oxidative dehydrogenation at room temperature
    Wang, Zhidong
    Fei, Guiqiang
    Shi, Sanshan
    Liu, Mengmeng
    Li, Peng
    Xie, Pan
    MOLECULAR CATALYSIS, 2024, 564
  • [30] A Visible-Light-Driven Molecular Motor Based on Pyrene
    Roke, Diederik
    Feringa, Ben L.
    Wezenberg, Sander J.
    HELVETICA CHIMICA ACTA, 2019, 102 (02)