Electrolytic partial fluorination of organic compounds. 42. Marked solvent effects on regioselective anodic monofluorination of 4-oxo-2-pyrimidyl sulfides

被引：44

作者：

Shaaban, MR ^{[1
]}

Ishii, H ^{[1
]}

Fuchigami, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Elect Chem, Midori Ku, Yokohama, Kanagawa 2268502, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 25期

关键词：

D O I：

10.1021/jo001129u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective anodic monofluorination of 4-oxo-2-pyrimidyl sulfides was investigated under various electrolytic conditions. Anodic fluorination was successfully carried out using Et4NF.4HF in dimethoxyethane (DME) to provide the corresponding alpha -fluorinated products in good yields. In contrast, acetonitrile (MeCN) was not suitable for the anodic fluorination due to the severe anode passivation during the electrolysis. A mixed solvent of DME and MeCN was found to be also effective for the fluorination, and the product yield increased with an increase of the ratio of DME to MeCN. The superiority of DME can be explained mainly in terms of the suppression of the anode passivation and enhancement of the nucleophilicity of the fluoride ions. Such marked solvent effects on the anodic fluorination were discussed in detail.

引用

页码：8685 / 8689

页数：5

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