Palladium-Catalyzed Electrooxidative Hydrofluorination of Aryl-Substituted Alkenes with a Nucleophilic Fluorine Source

被引:10
|
作者
Mandal, Anup [1 ]
Jang, Jieun [1 ]
Yang, Baeho [1 ]
Kim, Hyunwoo [2 ]
Shin, Kwangmin [1 ]
机构
[1] Sungkyunkwan Univ, Dept Chem, Suwon 16419, South Korea
[2] Pohang Univ Sci & Technol POSTECH, Dept Chem, Pohang 37673, South Korea
基金
新加坡国家研究基金会;
关键词
C-H FLUORINATION; ELECTROCHEMICAL FLUORINATION;
D O I
10.1021/acs.orglett.2c04045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report an electrocatalytic hydrofluorination of aryl-substituted alkenes with a nucleophilic fluorine source. The merger of palladium catalysis with electrooxidation enables the transformation of various substrates ranging from styrenes to more challenging alpha,beta-unsaturated carbonyl derivatives to the corresponding benzylic fluorides. This method can also be applied to the late-stage modification of pharmaceutical derivatives. Mechanistic studies suggest that the generation of a high-valent palladium intermediate via anodic oxidation is the crucial step in this electrocatalytic hydrofluorination.
引用
收藏
页码:195 / 199
页数:5
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