Electrolytic partial fluorination of organic compounds. 24. Highly regioselective anodic monofluorination of 2-benzothiazolyl and 5-chloro-2-benzothiazolyl sulfides

被引:20
作者
Hou, YK [1 ]
Higashiya, S [1 ]
Fuchigami, T [1 ]
机构
[1] Tokyo Inst Technol, Dept Elect Chem, Midori Ku, Yokohama, Kanagawa 226, Japan
关键词
D O I
10.1021/jo971293q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Electrochemical fluorination of 2-benzothiazolyl and 5-chloro-2-benzothiazolyl sulfides was successfully carried out using Et4NF . 3HF as a supporting electrolyte and fluoride ion source in dimethoxyethane to provide the corresponding alpha-monofluorinated sulfides in good yields. Fluorination took place selectively at the position or to the sulfur atom of the sulfides, and the heterocyclic moieties were not fluorinated at all.
引用
收藏
页码:9173 / 9176
页数:4
相关论文
共 42 条
[1]  
[Anonymous], 1991, Fluorine in Bioorganic Chemistry
[2]  
ANTONOVA A, 1989, IZV KHIM, V22, P158
[3]   OXIDATIVE FLUORINATION OF SULFIDES IN PRESENCE OF ET3N.3HF [J].
BRIGAUD, T ;
LAURENT, E .
TETRAHEDRON LETTERS, 1990, 31 (16) :2287-2290
[4]  
Childs W. V., 1991, ORGANIC ELECTROCHEMI
[5]  
DAMOCO JJ, 1984, Patent No. 4448399
[6]   STUDIES ON ALKYLHETEROAROMATIC COMPOUNDS - THE REACTIVITY OF ALKYL POLYFUNCTIONALLY SUBSTITUTED AZINES TOWARDS ELECTROPHILIC REAGENTS [J].
ELNAGDI, MH ;
ABDELRAZEK, FM ;
IBRAHIM, NS ;
ERIAN, AW .
TETRAHEDRON, 1989, 45 (11) :3597-3604
[7]   ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .19. A NOVEL SYNTHESIS OF FLUOROTHIENO[2,3-B]PYRIDINES USING ANODIC FLUORINATION OF HETEROCYCLIC SULFIDES AS A KEY STEP [J].
ERIAN, AW ;
KONNO, A ;
FUCHIGAMI, T .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7654-7659
[8]  
FILLER R, 1992, ORGANOFLUORINE COMPO
[9]  
Filler R., 1982, Biomedicinal Aspects of Fluorine Chemistry
[10]   ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .4. REGIOSELECTIVE ANODIC MONOFLUORINATION OF 4-THIAZOLIDINONES AND ITS APPLICATION TO THE SYNTHESIS OF MONOFLUORO BETA-LACTAMS [J].
FUCHIGAMI, T ;
NARIZUKA, S ;
KONNO, A .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3755-3757