Decarboxylative fluorination of β-Ketoacids with N-fluorobenzenesulfonimide (NFSI) for the synthesis of α-fluoroketones: Substrate scope and mechanistic investigation

被引：13

作者：

Zhang, Rui ^{[1
]}

Ni, Chuanfa ^{[1
]}

He, Zhengbiao ^{[1
]}

Hu, Jinbo ^{[1
]}

机构：

[1] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Chinese Acad Sci, Key Lab Organofluorine Chem, 345 Ling Ling Rd, Shanghai 200032, Peoples R China

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2017年 / 203卷

基金：

中国国家自然科学基金;

关键词：

Decarboxylative fluorination; NFSI; beta-ketoacids; alpha-fluoroketones; BOND-FORMING REACTIONS; CARBOXYLIC-ACIDS; KETONES; TRIFLUOROMETHYLATION; HF;

D O I：

10.1016/j.jfluchem.2017.08.010

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Cesium carbonate (Cs2CO3)-mediated decarboxylative fluorination of beta-ketoacids using NFSI in the MeCN/H2O mixed solvent system affords alpha-fluoroketones with a broad scope. Both electron-rich and electron-deficient alpha-non-substituted beta-ketoacids are amenable to this protocol. The mechanistic study indicates that the reaction proceeds through electrophilic fluorination followed by decarboxylation, which is different from the decarboxylative fluorination of normal carboxylic acids.

引用

页码：166 / 172

页数：7

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