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.
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页数：6
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