The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives

被引：12

作者：

Kuribayashi, Shunsuke ^{[1
]}

Kurioka, Tomoyuki ^{[2
]}

Inagi, Shinsuke ^{[2
]}

Lu, Ho-Jung ^{[3
]}

Uang, Biing-Jiun ^{[3
]}

Fuchigami, Toshio ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Elect Chem, Midori Ku, 4259 Nagatsuta Cho, Yokohama, Kanagawa 2268502, Japan

[2] Tokyo Inst Technol, Sch Mat & Chem Technol, Dept Chem Sci & Engn, Midori Ku, 4259 Nagatsuta Cho, Yokohama, Kanagawa 2268502, Japan

[3] Natl Tsing Hua Univ, Dept Chem, 101,Sec 2,Kuang Fu Rd, Hsinchu 300, Taiwan

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 14卷

关键词：

anodic cyclization; diastereoselective fluorination; electrosynthesis; fluorobenzothiophenone; selective fluorination; ELECTROLYTIC PARTIAL FLUORINATION; REGIOSELECTIVE ANODIC FLUORINATION; ORGANIC-COMPOUNDS; FLUOROORGANIC COMPOUNDS; HETEROCYCLIC SULFIDES; SULFUR; METHOXYLATION; THIOESTERS; ACIDS; MONOFLUORINATION;

D O I：

10.3762/bjoc.14.27

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We herein report that the regioselective anodic fluorination of S-alkyl benzothioate and its derivatives in various aprotic solvents using Et3N center dot nHF (n = 3-5) and Et4NF center dot nHF (n = 3-5) as supporting electrolyte and a fluorine source successfully provided the corresponding alpha-fluorinated products in moderate yields. Dichloromethane containing Et4NF center dot 4HF was found to be the most suitable combination as electrolytic solvent and supporting salt as well as fluorine source for the anodic fluorination. The electrochemical fluorination of cyclic benzothioates such as benzothiophenone was also achieved.

引用

页码：389 / 396

页数：8

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