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
  • [41] Visible-Light-Induced Dual Acylation of Alkenes for the Construction of 3-Substituted Chroman-4-ones
    Liu, Yi-Chen
    Chen, Pu
    Li, Xue-Jiao
    Xiong, Bi-Quan
    Liu, Yu
    Tang, Ke-Wen
    Huang, Peng-Fei
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (06): : 4263 - 4272
  • [42] Visible-Light-Induced Aerobic Oxidative Csp3-H Functionalization of Glycine Derivatives for 2-Substituted Benzoxazoles
    Zhu, Zhi-Qiang
    Liu, Shan
    Hu, Zhi-Yu
    Xie, Zong-Bo
    Tang, Juan
    Le, Zhang-Gao
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (10) : 2568 - 2572
  • [43] Visible-light-induced intramolecular sp3 C-H oxidation of 2-alkyl-substituted benzamides for the synthesis of functionalized iminoisobenzofurans
    Wu, Lingang
    Hao, Yanan
    Liu, Yuxiu
    Wang, Qingmin
    CHEMICAL COMMUNICATIONS, 2019, 55 (92) : 13908 - 13911
  • [44] Visible-light-induced ligand-free RuCl3 catalyzed C-H phosphorylation in water
    Gou, Xue-Ya
    Zhang, Bo-Sheng
    Wang, Xin-Gang
    Shi, Wei-Yu
    Liu, Hong-Chao
    An, Yang
    Zhang, Zhe
    Liang, Yong-Min
    CHEMICAL COMMUNICATIONS, 2020, 56 (34) : 4704 - 4707
  • [45] Photocatalytic Visible-Light-Induced Nitrogen Insertion via Dual C(sp3)-H and C(sp2)-H Bond Functionalization: Access to Privileged Imidazole-based Scaffolds
    Patel, Srilaxmi M.
    Prasad, Ermiya P.
    Bakthadoss, Manickam
    Sharada, Duddu S.
    ORGANIC LETTERS, 2021, 23 (02) : 257 - 261
  • [46] Visible-Light-Induced C-H Functionalization and C-C/C-X Bond-Forming Oxidative Cross-Coupling Reactions
    Zhang, Heng
    Lei, Aiwen
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (07) : 1164 - 1177
  • [47] Functionalization of DNA-Tagged Alkenes Enabled by Visible-Light-Induced C-H Activation of N-Aryl Tertiary Amines
    Wu, Rongfeng
    Du, Tian
    Sun, Wenbo
    Shaginian, Alex
    Gao, Sen
    Li, Jin
    Wan, Jinqiao
    Liu, Guansai
    ORGANIC LETTERS, 2021, 23 (09) : 3486 - 3490
  • [48] Visible-light-induced Csp3-H functionalization of glycine derivatives by cerium catalysis
    Wang, Shutao
    Ye, Yanjie
    Hu, Yansong
    Meng, Xu
    Liu, Zhao
    Liu, Jiyu
    Chen, Kuan
    Zhang, Zhengze
    Zhang, Yuan
    CHEMICAL COMMUNICATIONS, 2023, 59 (18) : 2628 - 2631
  • [49] Metal- and photocatalyst-free visible-light-promoted regioselective selenylation of coumarin derivatives via oxidation-induced C-H functionalization
    Yang, Daoshan
    Li, Guoqing
    Xing, Chengyu
    Cui, Wenwen
    Li, Kexin
    Wei, Wei
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (20): : 2974 - 2979
  • [50] Direct C-H Functionalization of Enamides and Enecarbamates by Using Visible-Light Photoredox Catalysis
    Jiang, Heng
    Huang, Chengmei
    Guo, Jiajia
    Zeng, Chuanqi
    Zhang, Yan
    Yu, Shouyun
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (47) : 15158 - 15166