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
  • [31] C-H Fluoromethoxylation of Arenes by Photoredox Catalysis
    Bertoli, Giulia
    Martinez, Angel Manu
    Goebel, Jonas F.
    Belmonte, Debora
    Sivendran, Nardana
    Goossen, Lukas J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (05)
  • [32] Recent Advances in C-H Functionalisation through Indirect Hydrogen Atom Transfer
    Meger, Filip S.
    Murphy, John A.
    Aldabbagh, Fawaz
    MOLECULES, 2023, 28 (16):
  • [33] Direct C-H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis
    Tomita, Ren
    Yasu, Yusuke
    Koike, Takashi
    Akita, Munetaka
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 1099 - 1106
  • [34] Easy access to drug building-blocks through benzylic C-H functionalization of phenolic ethers by photoredox catalysis
    Brandhofer, Tobias
    Stinglhamer, Martin
    Derdau, Volker
    Mendez, Maria
    Poeverlein, Christoph
    Garcia Mancheno, Olga
    CHEMICAL COMMUNICATIONS, 2021, 57 (55) : 6756 - 6759
  • [35] Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration
    Capaldo, Luca
    Ravelli, Davide
    Fagnoni, Maurizio
    CHEMICAL REVIEWS, 2022, 122 (02) : 1875 - 1924
  • [36] Controlling selectivity of hydrogen atom transfer (HAT) in photoredox catalysis
    Funes-Ardoiz, Ignacio
    Garrido-Barros, Pablo
    CHEM CATALYSIS, 2024, 4 (03):
  • [37] Direct Radiofluorination of Arene C-H Bonds via Photoredox Catalysis Using a Peroxide as the Terminal Oxidant
    Wang, Li
    White, Alexander R.
    Chen, Wei
    Wu, Zhanhong
    Nicewicz, David A.
    Li, Zibo
    ORGANIC LETTERS, 2020, 22 (20) : 7971 - 7975
  • [38] Synthesis of Ketodeoxysugars from Acylated Pyranosides Using Photoredox Catalysis and Hydrogen Atom Transfer
    Turner, Julia A.
    Rosano, Nicholas
    Gorelik, Daniel J.
    Taylor, Mark S.
    ACS CATALYSIS, 2021, 11 (17) : 11171 - 11179
  • [39] Aliphatic C-H alkylation via photoredox catalysis
    Morton, Carla
    Choi, Gilbert
    Zhu, Qilei
    Knowles, Robert
    Alexanian, Erik
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [40] Hydrogen Atom Transfer for C(sp3)-H Functionalization Enabled by Photoredox/Thianthrene/Methanol Synergistic Catalysis
    Zhang, Xiaoyi
    Ning, Shen
    Li, Yi
    Xiong, Yanjiao
    Wu, Xuesong
    CHEMCATCHEM, 2023, 15 (11)
12345