Electrolytic partial fluorination of organic compounds .22. Highly regioselective anodic monofluorination of oxindole and 3-oxo-1,2,3,4-tetrahydroisoquinoline derivatives: Effects of supporting fluoride salts and anode materials

被引：32

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 25期

关键词：

D O I：

10.1021/jo971173i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly regioselective monofluorination of 1-aryl-3-(phenylthio)oxindoles and 2-substituted-3-oxo-4-(phenylthio)-1,2,3,4-tetrahydroisoquinolines can be successfully carried out in the presence of Me4NF . 4HF or Et4NF . 3HF as a supporting electrolyte to provide the corresponding S-fluorinated oxindole and 4-fluorinated isoquinoline derivatives in good yields. Carbon anodes as well as a platinum anode were found to be effective for the fluorination when Me4NF . 4HF was used as the supporting electrolyte.

引用

页码：8773 / 8776

页数：4

共 35 条

[1]

[Anonymous], 1991, Fluorine in Bioorganic Chemistry

[2] ELECTROCHEMICAL MONOFLUORINATION OF PYRIDINE - SYNTHESIS OF 2-FLUOROPYRIDINE AT A PLATINUM ANODE [J].

BALLINGER, JR ;

TEARE, FW ;

BOWEN, BM ;

GARNETT, ES .

ELECTROCHIMICA ACTA, 1985, 30 (08) :1075-1077

[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] 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

[6]

Filler R., 1982, BIOMEDICAL ASPECTS F

[7] 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

[8] Highly selective electrochemical fluorination of organic compounds [J].

Fuchigami, T ;

Konno, A .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1997, 55 (04) :301-312

[9] ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .1. REGIOSELECTIVE ANODIC MONOFLUORINATION OF ORGANOSULFUR COMPOUNDS [J].

FUCHIGAMI, T ;

SHIMOJO, M ;

KONNO, A ;

NAKAGAWA, K .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6074-6075

[10] ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .12. SELECTIVE ANODIC MONOFLUORINATION OF FLUOROALKYL AND ALKYL SULFIDES [J].

FUCHIGAMI, T ;

KONNO, A ;

NAKAGAWA, K ;

SHIMOJO, M .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5937-5941

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