Direct C-H Multifluoroarylation of Ethers through Hydrogen Atom Transfer Using Photoredox Catalysis

被引：27
|
作者：
Wang, Junlei [1 ]
Huang, Binbin [1 ]
Gao, Yuan [2 ]
Yang, Chao [1 ]
Xia, Wujiong [1 ]
机构：
[1] Harbin Inst Technol Shenzhen, State Key Lab Urban Water Resource & Environm, Shenzhen 518055, Peoples R China
[2] Yantai Univ, Sch Chem & Chem Engn, 30 Qingquan RD, Laishan Dist 264005, Yantai, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 11期
关键词：
BOND ACTIVATION; AROMATIC-SUBSTITUTION; ARYL CHLORIDES; FACILE ACCESS; F BOND; NICKEL; ELECTRON; FLUORINE; HYDRODEFLUORINATION; ALKYLATION;
D O I：
10.1021/acs.joc.9b00708
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A direct defluorinative multifluoroarylation of unactivated sp(3) C-H bonds through hydrogen atom transfer using photoredox catalysis has been developed. The C(sp(3))-C(sp(2)) couplings between C(sp(2))-F bonds and corresponding C(sp(3))-H bonds adjacent to heteroatoms proceeded smoothly to afford the desired products in moderate to good yields. Preliminary mechanistic investigations on this novel transformation revealed that the C-H cleavage process might be involved in the rate determining step.
引用
收藏
页码：6895 / 6903
页数：9
相关论文
共 50 条
  • [41] Enantioselective Cyanation of Remote C-H Bonds via Cooperative Photoredox and Copper Catalysis
    Cheng Zhongming
    Chen Pinhong
    Liu Guosheng
    ACTA CHIMICA SINICA, 2019, 77 (09) : 856 - 860
  • [42] Photoredox Catalysis-Enabled C-H Difluoromethylation of Heteroarenes with Pentacoordinate Phosphorane as the Reagent
    Song, Huanhuan
    Li, Jingwen
    Zhang, Yinbin
    Chen, Ke
    Liu, Le
    Zhang, Junjie
    Duan, Xin-Hua
    Hu, Mingyou
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (16) : 12013 - 12023
  • [43] Visible light photoredox-catalysed remote C-H functionalisation enabled by 1,5-hydrogen atom transfer (1,5-HAT)
    Guo, Weisi
    Wang, Qian
    Zhu, Jieping
    CHEMICAL SOCIETY REVIEWS, 2021, 50 (13) : 7359 - 7377
  • [44] Dehydrogenative Silylation of Alkenes for the Synthesis of Substituted Allylsilanes by Photoredox, Hydrogen-Atom Transfer, and Cobalt Catalysis
    Yu, Wan-Lei
    Luo, Yong-Chun
    Yan, Lei
    Liu, Dan
    Wang, Zhu-Yin
    Xu, Peng-Fei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (32) : 10941 - 10945
  • [45] Direct allylic acylation via cross-coupling involving cooperative N-heterocyclic carbene, hydrogen atom transfer, and photoredox catalysis
    Wang, Xiaochen
    Yang, Rongxin
    Zhu, Binbing
    Liu, Yuxiu
    Song, Hongjian
    Dong, Jianyang
    Wang, Qingmin
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [46] Triarylamine-based porous coordination polymers performing both hydrogen atom transfer and photoredox catalysis for regioselective α-amino C(sp3)-H arylation
    Li, Hanning
    Yang, Yang
    Jing, Xu
    He, Cheng
    Duan, Chunying
    CHEMICAL SCIENCE, 2021, 12 (24) : 8512 - 8520
  • [47] Stereo- and Enantioselective Benzylic C-H Alkenylation via Photoredox/Nickel Dual Catalysis
    Cheng, Xiaokai
    Li, Tongtong
    Liu, Yuting
    Lu, Zhan
    ACS CATALYSIS, 2021, 11 (17) : 11059 - 11065
  • [48] Design of Organic Radical Cations as Potent Hydrogen-Atom Transfer Catalysts for C-H Functionalization
    Matsumoto, Akira
    Maruoka, Keiji
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (04)
  • [49] Cerium-Catalyzed C-H Functionalizations of Alkanes Utilizing Alcohols as Hydrogen Atom Transfer Agents
    An, Qing
    Wang, Ziyu
    Chen, Yuegang
    Wang, Xin
    Zhang, Kaining
    Pan, Hui
    Liu, Weimin
    Zuo, Zhiwei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (13) : 6216 - 6226
  • [50] Difluoroalkylation/C-H Annulation Cascade Reaction Induced by Visible-Light Photoredox Catalysis
    Li, Jin
    Chen, Jingzhi
    Jiao, Wei
    Wang, Guoqiang
    Li, Ying
    Cheng, Xu
    Li, Guigen
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (20) : 9992 - 10001
12345