C-H Fluoromethoxylation of Arenes by Photoredox Catalysis

被引：17
|
作者：
Bertoli, Giulia [1 ]
Martinez, Angel Manu [1 ]
Goebel, Jonas F. [1 ]
Belmonte, Debora [1 ]
Sivendran, Nardana [1 ]
Goossen, Lukas J. [1 ]
机构：
[1] Ruhr Univ Bochum, Fak Chem & Biochem, Univ Str 150, D-44801 Bochum, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 05期
关键词：
Electrosynthesis; Fluorine; Monofluoromethyl; Photochemistry; Radical Reactions; ALIPHATIC CARBOXYLIC-ACIDS; PERIPHERAL BENZODIAZEPINE-RECEPTOR; DECARBOXYLATIVE FLUORINATION; ELECTROPHILIC MONOFLUOROMETHYLATION; FLUOROMETHYL ETHERS; ROOM-TEMPERATURE; VIVO EVALUATION; FLUORODECARBOXYLATION; F-18; NUCLEOPHILES;
D O I：
10.1002/anie.202215920
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Redox-active N-(fluoromethoxy)benzotriazoles were made accessible from fluoroacetic acid and hydroxybenzotriazoles via electrodecarboxylative coupling. After alkylation, they become effective monofluoromethoxylation reagents, enabling the photocatalytic C-H functionalization of arenes. Thus, irradiation of 1-(OCH2F)-3-Me-6-(CF3)benzotriazolium triflate with blue LED light in the presence of [Ru(bpy)(3)(PF6)(2)] promotes the synthesis of diversely functionalized aryl monofluoromethyl ethers. This method allows the late-stage functionalization of biologically relevant structures without relying on ecologically problematic halofluorocarbons.
引用
收藏
页数：6
相关论文
共 50 条
  • [1] Functionalization of C-H Bonds by Photoredox Catalysis
    Qin, Qixue
    Jiang, Heng
    Hu, Zhentao
    Ren, Daan
    Yu, Shouyun
    CHEMICAL RECORD, 2017, 17 (08) : 754 - 774
  • [2] Direct C-H Trifluoromethylation of Glycals by Photoredox Catalysis
    Wang, Bang
    Xiong, De-Cai
    Ye, Xin-Shan
    ORGANIC LETTERS, 2015, 17 (22) : 5698 - 5701
  • [3] 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
  • [4] Direct C-H Phosphonylation of Electron-Rich Arenes and Heteroarenes by Visible-Light Photoredox Catalysis
    Shaikh, Rizwan S.
    Ghosh, Indrajit
    Koenig, Burkhard
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (50) : 12120 - 12124
  • [5] Selective C-H trifluoromethylation of benzimidazoles through photoredox catalysis
    Gao, Guo-Lin
    Yang, Chao
    Xia, Wujiong
    CHEMICAL COMMUNICATIONS, 2017, 53 (06) : 1041 - 1044
  • [6] Metal-Free Direct C-H Perfluoroalkylation of Arenes and Heteroarenes Using a Photoredox Organocatalyst
    Cui, Lei
    Matusaki, Yoko
    Tada, Norihiro
    Miura, Tsuyoshi
    Uno, Bunji
    Itoh, Akichika
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) : 2203 - 2207
  • [7] Direct C-H difluoromethylation of heterocycles via organic photoredox catalysis
    Zhang, Wei
    Xiang, Xin-Xin
    Chen, Junyi
    Yang, Chen
    Pan, Yu-Liang
    Cheng, Jin-Pei
    Meng, Qingbin
    Li, Xin
    NATURE COMMUNICATIONS, 2020, 11 (01)
  • [8] Site-Selective C-H Acylation of Pyridinium Derivatives by Photoredox Catalysis
    Jung, Sungwoo
    Lee, Hyeonyeong
    Moon, Yonghoon
    Jung, Hoi-Yun
    Hong, Sungwoo
    ACS CATALYSIS, 2019, 9 (11): : 9891 - 9896
  • [9] Visible-Light-Promoted C-H Arylation by Merging Palladium Catalysis with Organic Photoredox Catalysis
    Jiang, Jian
    Zhang, Wen-Man
    Dai, Jian-Jun
    Xu, Jun
    Xu, Hua-Jian
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (07) : 3622 - 3630
  • [10] Exploiting photoredox catalysis for carbohydrate modification through C-H and C-C bond activation
    Shatskiy, Andrey
    Stepanova, Elena, V
    Karkas, Markus D.
    NATURE REVIEWS CHEMISTRY, 2022, 6 (11) : 782 - 805
12345