Visible-Light-Induced Radical Cyclization of Trifluoroacetimidoyl Chlorides with Alkynes: Catalytic Synthesis of 2-Trifluoromethyl Quinolines

被引:51
|
作者
Dong, Xichang [1 ]
Xu, Youwei [1 ]
Liu, Jing Jing [1 ]
Hu, Yumin [1 ]
Xiao, Tiebo [1 ]
Zhou, Lei [1 ]
机构
[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
cyclization; photocatalysis; quinolines; radicals; visible light; C-H FUNCTIONALIZATION; ALPHA-AMINOALKYL RADICALS; PHOTOREDOX CATALYSIS; EFFICIENT SYNTHESIS; ELECTRON-TRANSFER; ORGANIC-REACTIONS; IMIDOYL RADICALS; BOND FORMATIONS; AQUEOUS-MEDIA; TRIPLE BOND;
D O I
10.1002/chem.201303149
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and efficient method for the synthesis of 2-trifluoromethyl quinolines by means of visible-light-induced radical cyclization of trifluoroacetimidoyl chlorides with alkynes has been developed. This protocol allows the generation of imidoyl radicals by activation of C(sp 2)Cl bonds using a photoredox catalyst under mild and environmentally friendly conditions (see scheme). © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:16928 / 16933
页数:6
相关论文
共 50 条
  • [41] Visible-Light-Induced Cascade Radical Trifluoromethylation/Cyclization/Dearomatization of Isocyanide-Containing Indoles: Synthesis of Trifluoromethylated 3-Spiroindolines
    Lv, Yuyu
    Deng, Zhoubin
    Zhu, Zhijun
    Wang, Junjiao
    Wang, Ke-Hu
    Huang, Danfeng
    Hu, Yulai
    JOURNAL OF ORGANIC CHEMISTRY, 2024,
  • [42] Visible-light-induced synthesis of 2,4-disubstituted quinolines from o-vinylaryl isocyanides and oxime esters
    Liu, Yu
    Ding, Chuan
    Huang, Jia-Jing
    Zhou, Quan
    Xiong, Bi-Quan
    Tang, Ke-Wen
    Huang, Peng-Fei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (07) : 1458 - 1465
  • [43] Visible-Light-Induced Three-Component Radical Strategy for the Synthesis of β-Amino Alcohols
    Wu, Zhongtian
    Su, Kai
    Liu, Huiying
    Wang, Ze
    Wang, Zhaoshan
    Duan, Xiu
    Chen, Dong
    Feng, Jie
    Wu, Xinxin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [44] Visible-Light-Induced [4+2] Annulation of Thiophenes and Alkynes to Construct Benzene Rings
    Song, Chunlan
    Dong, Xin
    Wang, Zhongjie
    Liu, Kun
    Chiang, Chien-Wei
    Lei, Aiwen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (35) : 12206 - 12210
  • [45] Construction of 3,12-Diazatetracyclododecane-dienes through Unexpected Visible-Light-Induced Radical Cascade Cyclization
    Zhong, Qidi
    Wang, Yinxin
    Lan, Hanyang
    Zhu, Hao
    Fan, Qiangwen
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (16): : 10937 - 10946
  • [46] Visible-Light-Induced Atom Transfer Radical Addition and Cyclization of Perfluoroalkyl Halides with 1,n-Enynes
    Wang, Shuo-Wen
    Yu, Jian
    Zhou, Qin-Yi
    Chen, Si-Yu
    Xu, Zhen-Hua
    Tang, Shi
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (11) : 10154 - 10162
  • [47] Visible-light-induced radical cyclization of N-allylbenzamide with [Bis (difluoroacetoxy)iodo]benzene to difluoromethylated dihydroisoquinolinones
    Wang, Xiuxiu
    Liu, Ruiyue
    Zhang, Shuyue
    Zhou, Ting
    Zhao, Xia
    Lu, Kui
    TETRAHEDRON LETTERS, 2022, 96
  • [48] Visible-Light-Induced Tandem Radical Addition-Cyclization of Alkenyl Aldehydes Leading to Indanones and Related Compounds
    Lu, Danyang
    Wan, Yimei
    Kong, Lichun
    Zhu, Gangguo
    ORGANIC LETTERS, 2017, 19 (11) : 2929 - 2932
  • [49] Visible-Light-Induced Cyclization/Aromatization of 2-Vinyloxy Arylalkynes: Synthesis of Thio-Substituted Dibenzofuran Derivatives
    Chen, Hui
    Yan, Yunyun
    Zhang, Niuniu
    Mo, Zuyu
    Xu, Yanli
    Chen, Yanyan
    ORGANIC LETTERS, 2021, 23 (02) : 376 - 381
  • [50] Visible-light-induced cascade dearomatization cyclization between alkynes and indole-derived bromides: a facile strategy to synthesize spiroindolenines
    Gao, Xiaoshuang
    Yuan, Yao
    Xie, Xiaomin
    Zhang, Zhaoguo
    CHEMICAL COMMUNICATIONS, 2020, 56 (90) : 14047 - 14050