ELECTROCHEMICAL TRIFLUOROMETHYLATION OF OLEFINS - PRODUCT-SELECTIVITY AND MECHANISTIC ASPECTS

被引：42

作者：

UNEYAMA, K

机构：

[1] Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama

来源：

TETRAHEDRON | 1991年 / 47卷 / 4-5期

关键词：

D O I：

10.1016/S0040-4020(01)87045-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trifluoroacetic acid (TFA) can be converted almost quantitatively to the trifluoromethyl radicals by electrochemical oxidation of TFA. The electrolysis is conducted in an MeCN-H2O-(Pt) system using an undivided cell. The electrochemically generated CF3.radicals can attack mostly electron-deficient olefins leading to the trifluoromethylated carbon radicals of which chemical and electrochemical fate can be controlled by current density, reaction temperature, and substituents of olefins.

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页码：555 / 562

页数：8

相关论文

共 29 条

[1] OUTER-SPHERE DISSOCIATIVE ELECTRON-TRANSFER TO ORGANIC-MOLECULES - A SOURCE OF RADICALS OR CARBANIONS - DIRECT AND INDIRECT ELECTROCHEMISTRY OF PERFLUOROALKYL BROMIDES AND IODIDES [J].

ANDRIEUX, CP ;

GELIS, L ;

MEDEBIELLE, M ;

PINSON, J ;

SAVEANT, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3509-3520

[2] UNUSUAL REACTIONS RESULTING FROM THE ADDITION ON OLEFINS OF TRIFLUOROMETHYL RADICALS OBTAINED FROM DISSOCIATIVE ELECTRON-TRANSFER BETWEEN ELECTROCHEMICALLY GENERATED AROMATIC ANION RADICALS AND TRIFLUOROMETHYL BROMIDE [J].

ANDRIEUX, CP ;

GELIS, L ;

SAVEANT, JM .

TETRAHEDRON LETTERS, 1989, 30 (37) :4961-4964

[3] REACTIONS OF OLEFINIC DOUBLE-BONDS WITH POLYFLUOROALKYL RADICALS GENERATED ELECTROCHEMICALLY [J].

BROOKES, CJ ;

COE, PL ;

OWEN, DM ;

PEDLER, AE ;

TATLOW, JC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (09) :323-324

[4] REACTIONS OF FLUOROALKYL RADICALS GENERATED ELECTROCHEMICALLY .1. ADDITIONS OF TRIFLUOROMETHYL RADICALS TO OLEFINIC AND ACETYLENIC BONDS [J].

BROOKES, CJ ;

COE, PL ;

PEDLER, AE ;

TATLOW, JC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (03) :202-209

[5]

Filler R., 1982, BIOMEDICAL ASPECTS F

[6] REACTIONS OF BROMOTRIFLUOROMETHANE WITH ACID-DERIVATIVES IN THE PRESENCE OF ZINC [J].

FRANCESE, C ;

TORDEUX, M ;

WAKSELMAN, C .

TETRAHEDRON LETTERS, 1988, 29 (09) :1029-1030

[7]

Hudlicky M., 1976, CHEM ORGANIC FLUORIN

[8] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS BETWEEN ALLYL, VINYL OR ARYL HALIDE AND PERFLUOROALKYL IODIDE WITH ZINC AND ULTRASONIC IRRADIATION [J].

KITAZUME, T ;

ISHIKAWA, N .

CHEMISTRY LETTERS, 1982, (01) :137-140

[9] TRIFLUOROMETHYLATION OF CARBONYL-COMPOUNDS WITH TRIFLUOROMETHYL-ZINC IODIDE UNDER ULTRASONIC IRRADIATION [J].

KITAZUME, T ;

ISHIKAWA, N .

CHEMISTRY LETTERS, 1981, (12) :1679-1680

[10] ULTRASOUND-PROMOTED SELECTIVE PERFLUOROALKYLATION ON THE DESIRED POSITION OF ORGANIC-MOLECULES [J].

KITAZUME, T ;

ISHIKAWA, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (18) :5186-5191