Visible-light-induced photocatalytic difluoroalkylation of 3-substituted benzo[d]isoxazoles via direct and regioselective C-H functionalization

被引:8
|
作者
Hua, Ming-Qing [1 ]
Mou, Fang-You [1 ]
Wang, Nian-Hong [1 ]
Chen, Yan [1 ]
Xiong, Heng-Ying [3 ]
Huang, Yan [1 ]
Lei, Cheng-Lin [4 ]
Zhang, Qi [1 ,2 ]
机构
[1] Jiangsu Univ, Sch Chem & Chem Engn, Zhenjiang 212013, Jiangsu, Peoples R China
[2] Hainan Univ, Hainan Prov Key Lab Fine Chem, Haikou 570228, Hainan, Peoples R China
[3] Henan Univ, Coll Chem & Chem Engn, Kaifeng 475004, Henan, Peoples R China
[4] Shuangliang Ecoenergy Syst Co Ltd, Wuxi 214431, Peoples R China
基金
中国国家自然科学基金;
关键词
Difluoroalkylation; Benzo[d]isoxazoles; Visible-light photocatalysis; Site-selectivity; CASCADE DIFLUOROALKYLATION; CYCLIZATION; DESIGN; ACCESS; CARBONYLATION; BENZISOXAZOLE; DERIVATIVES; FLUORINE; ALKENES; ARENES;
D O I
10.1016/j.tetlet.2018.10.007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The difluoroalkylation of unactivated benzo[d]isoxazoles with ethyl difluorobromoacetate by visible-light photoredox catalysis via direct and regioselective C-H functionalization has been efficiently achieved under mild reaction conditions. The difluoroalkylated adducts could be readily converted to a variety of corresponding CF2-containing heterocycles, demonstrating the synthetic utility of the present approach. (C) 2018 Published by Elsevier Ltd.
引用
收藏
页码:4449 / 4453
页数:5
相关论文
共 50 条
  • [31] Visible light-induced direct α C–H functionalization of alcohols
    Linbin Niu
    Jiamei Liu
    Xing-An Liang
    Shengchun Wang
    Aiwen Lei
    Nature Communications, 10
  • [32] Visible-light-induced direct α-C(sp3)-H thiocyanation of tertiary amines
    Yadav, Arvind K.
    Yadav, Lal Dhar S.
    TETRAHEDRON LETTERS, 2015, 56 (48) : 6696 - 6699
  • [33] Direct C-H sulfenylation of quinoxalinones with thiols under visible-light-induced photocatalyst-free conditions
    Teng, Qing-Hu
    Yao, Yan
    Wei, Wen-Xiu
    Tang, Hai-Tao
    Li, Jia-Rong
    Pan, Ying-Ming
    GREEN CHEMISTRY, 2019, 21 (23) : 6241 - 6245
  • [34] Photocatalytic/Cu-Promoted C-H Activations: Visible-light-Induced ortho-Selective Perfluoroalkylation of Benzamides
    Chen, Xiang
    Tan, Ze
    Gui, Qingwen
    Hu, Liang
    Liu, Jidan
    Wu, Jing
    Wang, Guangwei
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (18) : 6218 - 6222
  • [35] Visible Light-Induced C-H Bond Functionalization: A Critical Review
    Revathi, Lekkala
    Ravindar, Lekkala
    Fang, Wan-Yin
    Rakesh, K. P.
    Qin, Hua-Li
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (24) : 4652 - 4698
  • [36] Visible-Light-Induced Selective α-Fluoroarylation of Secondary N-Alkyl Anilines with Polyfluoroarenes via Direct C-H/C-F Coupling
    Zhang, Hongchen
    Shao, Qi
    Zhang, Qiao
    Xia, Congjian
    Xu, Wengang
    Wu, Mingbo
    ORGANIC LETTERS, 2023, 25 (24) : 4556 - 4561
  • [37] Direct Benzylic C-H Functionalization with Fluorenones under Visible-Light Irradiation
    Zhao, Xi
    Yu, Xiaofeng
    Liu, Mingjun
    Huo, Yanping
    Ji, Shaomin
    Li, Xianwei
    Chen, Qian
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (04): : 2612 - 2620
  • [38] Visible-Light-Induced Regioselective ortho-C-H Phosphonylation of β-Naphthols with Diarylphosphine Oxides
    Yuan Jinwei
    Liu Yan
    Ge Yuanyuan
    Dong Shaoxuan
    Song Saiyi
    Yang Liangru
    Xiao Yongmei
    Zhang Shouren
    Qu Lingbo
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (12) : 4738 - 4748
  • [39] Visible-Light-Induced C-H Cyanoalkylation of Azauracils with Cycloketone Oxime Esters via Catalytic EDA Complex
    Huang, Xiao-Long
    Zhang, Dong-Liang
    Li, Qing
    Xie, Zong-Bo
    Le, Zhang-Gao
    Zhu, Zhi-Qiang
    ORGANIC LETTERS, 2024, 26 (18) : 3727 - 3732
  • [40] Regioselective and Direct Azidation of Anilines via Cu(II)-Catalyzed C-H Functionalization in Water
    Fang, Hongli
    Dou, Yandong
    Ge, Jingyan
    Chhabra, Mohit
    Sun, Hongyan
    Zhang, Pengfei
    Zheng, Yuguo
    Zhu, Qing
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (20): : 11212 - 11217