Visible light mediated intermolecular [3+2] annulation of cyclopropylanilines with alkynes

被引：48
作者：
Nguyen, Theresa H. [1 ]
Maity, Soumitra [1 ]
Zheng, Nan [1 ]
机构：
[1] Univ Arkansas, Dept Chem & Biochem, Fayetteville, AR 72701 USA
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 10卷
基金：
美国国家卫生研究院; 美国国家科学基金会;
关键词：
3+2; alkyne; annulation; cyclopropylaniline; photoredox catalysis; visible light; PHOTOREDOX CATALYSIS; TERTIARY AMINOCYCLOPROPANES; N-CYCLOPROPYLANILINES; MECHANISTIC PROBES; AEROBIC OXIDATION; RING; DERIVATIVES; RADICALS; ROUTES;
D O I：
10.3762/bjoc.10.96
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intermolecular [3 + 2] annulation of cyclopropylanilines with alkynes is realized using visible light photoredox catalysis, yielding a variety of cyclic allylic amines in fair to good yields. This method exhibits significant group tolerance particularly with heterocycles. It can also be used to prepare complex heterocycles such as fused indolines.
引用
收藏
页码：975 / 980
页数：6
相关论文
共 50 条
  • [41] Copper(II)-Mediated Intermolecular Radical [3+2]-Annulation of N,N-Dimethyl Enaminones: Direct Access to 5-Acyl-3-Furancarboxaldehydes
    Zhang, Biao
    Zhou, Pan
    Xu, Hui
    Huang, Jiuzhong
    Sun, Yulin
    Liu, Donghan
    Yu, Fuchao
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (18) : 4354 - 4359
  • [42] Lewis and Bronsted Acid Induced (3+2)-Annulation of Donor-Acceptor Cyclopropanes to Alkynes: Indene Assembly
    Rakhmankulov, Eduard R.
    Ivanov, Konstantin L.
    Budynina, Ekaterina M.
    Ivanova, Olga A.
    Chagarovskiy, Alexey O.
    Skvortsov, Dmitriy A.
    Latyshev, Gennadij V.
    Trushkov, Igor V.
    Melnikov, Mikhail Ya
    ORGANIC LETTERS, 2015, 17 (04) : 770 - 773
  • [43] Visible-Light-Mediated Intermolecular Radical Conjugate Addition for the Construction of Vicinal Quaternary Carbon Centers
    Li, Lei
    Fang, Lili
    Wu, Weiping
    Zhu, Jin
    ORGANIC LETTERS, 2020, 22 (14) : 5401 - 5406
  • [44] Visible light induced intermolecular [2+2]-cycloaddition reactions of 3-ylideneoxindoles through energy transfer pathway
    Zou, You-Quan
    Duan, Shu-Wen
    Meng, Xiang-Gao
    Hu, Xiao-Qiang
    Gao, Shuang
    Chen, Jia-Rong
    Xiao, Wen-Jing
    TETRAHEDRON, 2012, 68 (34) : 6914 - 6919
  • [45] Visible-light photoredox catalyzed synthesis of pyrroloisoquinolines via organocatalytic oxidation/[3+2] cycloaddition/oxidative aromatization reaction cascade with Rose Bengal
    Vila, Carlos
    Lau, Jonathan
    Rueping, Magnus
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 1233 - 1238
  • [46] Photoredox-Catalyzed [3+2] annulation of Aromatic Amides with Olefins via Iminium Intermediates
    Tang, Zhanyong
    Yao, Zhenying
    Yu, Yueyang
    Huang, Jialin
    Ma, Xiaoqiang
    Zhao, Xingda
    Chang, Zhe
    Zhao, Depeng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (52)
  • [47] Visible-Light-Induced Radical Cyclization of Trifluoroacetimidoyl Chlorides with Alkynes: Catalytic Synthesis of 2-Trifluoromethyl Quinolines
    Dong, Xichang
    Xu, Youwei
    Liu, Jing Jing
    Hu, Yumin
    Xiao, Tiebo
    Zhou, Lei
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (50) : 16928 - 16933
  • [48] Catalytic Asymmetric Intermolecular [3+2] Photocycloaddition of Cyclopropylamines with Electron-Deficient Olefins
    Dai, Yating
    Huang, Hongchun
    Liang, Shuangshuang
    Yin, Yanli
    Ban, Xu
    Zhao, Xiaowei
    Jiang, Zhiyong
    ORGANIC LETTERS, 2023, 25 (24) : 4551 - 4555
  • [49] Visible-Light-Induced Formation of Thiavinyl 1,3-Dipoles: A Metal-Free [3+2] Oxidative Cyclization with Alkynes as Easy Access to Thiophenes
    Zheng, Baihui
    Li, Xiaotong
    Song, Yang
    Meng, Shuyang
    Li, Yifei
    Liu, Qun
    Pan, Ling
    ORGANIC LETTERS, 2021, 23 (09) : 3453 - 3459
  • [50] Catalytic Enantiospecific [3+2] Annulation of Aminocyclopropanes with Ketones
    Benfatti, Fides
    de Nanteuil, Florian
    Waser, Jerome
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (16) : 4844 - 4849
12345