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
  • [21] Reductive Amination by Photoredox Catalysis and Polarity-Matched Hydrogen Atom Transfer
    Guo, Xingwei
    Wenger, Oliver S.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (09) : 2469 - 2473
  • [22] The Dual Role of Benzophenone in Visible-Light/Nickel Photoredox-Catalyzed C-H Arylations: Hydrogen-Atom Transfer and Energy Transfer
    Dewanji, Abhishek
    Krach, Patricia E.
    Rueping, Magnus
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (11) : 3566 - 3570
  • [23] Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct α-Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis
    Twilton, Jack
    Christensen, Melodie
    DiRocco, Daniel A.
    Ruck, Rebecca T.
    Davies, Ian W.
    MacMillan, David W. C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (19) : 5369 - 5373
  • [24] β C-H di-halogenation via iterative hydrogen atom transfer
    Wappes, Ethan A.
    Vanitcha, Avassaya
    Nagib, David A.
    CHEMICAL SCIENCE, 2018, 9 (19) : 4500 - 4504
  • [25] Regioselective Arene C-H Alkylation Enabled by Organic Photoredox Catalysis
    Holmberg-Douglas, Natalie
    Onuska, Nicholas P. R.
    Nicewicz, David A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (19) : 7425 - 7429
  • [26] Photoinduced Hydrogen Atom Transfer Activation of Benzylic C-H Bonds Functionalization
    Guo, Guozhe
    Li, Wenduo
    ADVANCED SYNTHESIS & CATALYSIS, 2025,
  • [27] Photoredox-catalyzed direct C-H monofluoromethylation of heteroarenes
    Ramkumar, Nagarajan
    Plantus, Ketrina
    Ozola, Melita
    Mishnev, Anatoly
    Nikolajeva, Vizma
    Senkovs, Maris
    Oseka, Maksim
    Veliks, Janis
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (44) : 20642 - 20652
  • [28] Hydrogen Atom Transfer Reactions in Photocatalysis: Recent Advances in C-H Activation
    Santos, Bruno M. da S.
    Dupim, Mariana dos S.
    Oliveira, Pedro H. R.
    Finelli, Fernanda G.
    REVISTA VIRTUAL DE QUIMICA, 2021, 13 (02) : 509 - 539
  • [29] C-H allylation of N-aryl-tetrahydroisoquinolines by merging photoredox catalysis with iodide catalysis
    Feng, Zhujia
    Zeng, Tingting
    Xuan, Jun
    Liu, Yunhang
    Lu, Liangqiu
    Xiao, Wen-Jing
    SCIENCE CHINA-CHEMISTRY, 2016, 59 (02) : 171 - 174
  • [30] Efficiency and Selectivity Aspects in the C-H Functionalization of Aliphatic Oxygen Heterocycles by Photocatalytic Hydrogen Atom Transfer
    Raviola, Carlotta
    Ravelli, Davide
    SYNLETT, 2019, 30 (07) : 803 - 808
12345