Photocatalytic C-H Trifluoroethoxylation of (Hetero)arenes

被引:0
|
作者
Chen, Mingxi [1 ]
Ling, Jingjing [1 ]
Cheng, Keguang [1 ,2 ]
Wang, Quande [1 ]
机构
[1] Guangxi Normal Univ, Collaborat Innovat Ctr Guangxi Ethn Med, State Key Lab Chem & Mol Engn Med Resources, Key Lab Chem & Mol Engn Med Resources,Minist Educ, Guilin 541004, Peoples R China
[2] China Pharmaceut Univ, State Key Lab Nat Med, Nanjing 211198, Jiangsu, Peoples R China
关键词
PALLADIUM-CATALYZED 2,2,2-TRIFLUOROETHOXYLATION; BOND FORMATION; ARYL; FACILE; ETHERS; ACCESS; ARENES; ACIDS;
D O I
10.1021/acs.orglett.5c00383
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The trifluoroethoxy group (OCH2CF3) is a valuable motif prevalent in pharmaceuticals and agrichemicals. Herein, we present a simple radical trifluoroethoxylation method that enables nondirected functionalization of C-H bonds of a broad array of substrates, providing access to (hetero)aryl trifluoroethyl ethers. The current protocol tolerates a variety of synthetically and pharmacologically relevant functional groups. Applicability is also demonstrated through the late-stage functionalization of biorelevant molecules and marketing drugs.
引用
收藏
页码:2241 / 2246
页数:6
相关论文
共 50 条
  • [31] Electrophotocatalytic C-H Heterofunctionalization of Arenes
    Huang, He
    Lambert, Tristan H.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (20) : 11163 - 11167
  • [32] Recent Progress in Iridium-Catalyzed Remote Regioselective C-H Borylation of (Hetero)Arenes
    Zou, Xiaoliang
    Xu, Senmiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (07) : 2610 - 2620
  • [33] Late-Stage C-H Deuteration of (Hetero)Arenes via Deuterium-Bonding Enhanced Rhenium Catalysis
    Hu, Liqun
    Xiang, Yao
    Huang, Qing
    Zhou, Hui
    Xie, Youwei
    ACS CATALYSIS, 2025, : 4711 - 4718
  • [34] CF3-Carbenoid C-H Functionalization of (Hetero)arenes under Chelation-Controlled RhIII Catalysis
    Iagafarova, Irina E.
    Vorobyeva, Daria V.
    Peregudov, Alexander S.
    Osipov, Sergey N.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (22) : 4950 - 4955
  • [35] Facilitating Rh-Catalyzed C-H Alkylation of (Hetero)arenes and 6-Arylpurine Nucleosides (Nucleotides) with Electrochemistry
    Yang, Qi-Liang
    Liu, Ying
    Liang, Lei
    Li, Zhi-Hao
    Qu, Gui-Rong
    Guo, Hai-Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (09) : 6161 - 6178
  • [36] Photocatalytic C-H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow
    Wen, Zhenghui
    Wan, Ting
    Vijeta, Arjun
    Casadevall, Carla
    Buglioni, Laura
    Reisner, Erwin
    Noel, Timothy
    CHEMSUSCHEM, 2021, 14 (23) : 5265 - 5270
  • [37] Mechanistic studies on intramolecular C-H trifluoromethoxylation of (hetero)arenes via OCF3-migration
    Lee, Katarzyna N.
    Lei, Zhen
    Morales-Rivera, Cristian A.
    Liu, Peng
    Ngai, Ming-Yu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (24) : 5599 - 5605
  • [38] Direct C-H Bond Borylation of (Hetero)Arenes: Evolution from Noble Metal to Metal Free
    Li, Yahui
    Wu, Xiao-Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (05) : 1770 - 1774
  • [39] Introduction of Fluorinated Groups via Photoredox-Catalyzed C-H Functionalization of (Hetero-)Arenes
    Goebel, Jonas F.
    Manna, Sourav
    Satta, Pierpaolo
    Tzouras, Nikolaos V.
    Goossen, Lukas J.
    SYNLETT, 2024, 35 (20) : 2378 - 2384
  • [40] Transition-Metal-Catalyzed Direct C-H Alkenylation, Alkynylation, Benzylation, and Alkylation of (Hetero)arenes
    Messaoudi, Samir
    Brion, Jean-Daniel
    Alami, Mouad
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (34) : 6495 - 6516