Chemo-, Regio-, and Stereoselective Trifluoromethylation of Styrenes via Visible Light-Driven Single-Electron Transfer (SET) and Triplet-Triplet Energy Transfer (TTET) Processes

被引:115
|
作者
Lin, Qing-Yu [1 ]
Xu, Xiu-Hua [1 ]
Qing, Feng-Ling [1 ,2 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 21期
基金
中国国家自然科学基金;
关键词
COPPER-CATALYZED TRIFLUOROMETHYLATION; ALPHA; BETA-UNSATURATED CARBOXYLIC-ACIDS; C-H TRIFLUOROMETHYLATION; PHOTOREDOX CATALYSIS; RADICAL TRIFLUOROMETHYLATION; 3-COMPONENT OXYTRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; OLEFINIC TRIFLUOROMETHYLATION; MEDIATED TRIFLUOROMETHYLATION; BETA-TRIFLUOROMETHYLSTYRENES;
D O I
10.1021/jo502040t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A process for tunable and chemo-, regio-, and stereoselective photocatalytic trifluoromethylation of styrenes was developed. Thermodynamically stable E-trifluoromethylated alkenes were prepared using Tognis reagent in the presence of Ru(bpy)(3)Cl-2 center dot 6H(2)O under visible light irradiation, whereas less thermodynamically stable Z-trifluoromethylated alkenes were obtained by employing Umemotos reagent and photocatalyst Ir(ppy)(3).
引用
收藏
页码:10434 / 10446
页数:13
相关论文
共 7 条
  • [1] Amplifying dual-visible-light photoswitching in aqueous media via confinement promoted triplet-triplet energy transfer
    Wang, Wenhui
    Yang, Weixin
    Zhang, Zhiwei
    Dai, Jinghong
    Xu, Yisheng
    Zhang, Junji
    CHEMICAL SCIENCE, 2024, 15 (15) : 5539 - 5547
  • [2] Visible light-driven dearomative meta-cycloadditions of 2-acetonaphthalenes via triplet energy transfer cascade
    Rai, Pramod
    Naik, Sanghamitra
    Gupta, Kriti
    Maji, Kakoli
    Jindal, Garima
    Maji, Biplab
    NATURE COMMUNICATIONS, 2025, 16 (01)
  • [3] Light-Driven Single-Electron Transfer Processes as an Enabling Principle in Sulfur and Selenium Multicatalysis
    Breder, Alexander
    Depken, Christian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (48) : 17130 - 17147
  • [4] Organobismuth Compounds as Aryl Radical Precursors via Light-Driven Single-Electron Transfer
    Chiappini, Nicholas D.
    Geunes, Eric P.
    Bodak, Ethan T.
    Knowles, Robert R.
    ACS CATALYSIS, 2024, 14 (04) : 2664 - 2670
  • [6] Visible-light-driven radical Friedlander hetero-annulation of 2-aminoaryl ketone and α-methylene carbonyl compound via organic dye fluorescein through a single-electron transfer (SET) pathway
    Mohamadpour, Farzaneh
    BMC CHEMISTRY, 2022, 16 (01)
  • [7] Visible-light-driven radical Friedländer hetero-annulation of 2-aminoaryl ketone and α-methylene carbonyl compound via organic dye fluorescein through a single-electron transfer (SET) pathway
    Farzaneh Mohamadpour
    BMC Chemistry, 16