Electrochemical fluorination of β-dicarbonyl compounds using p-iodotoluene difluoride as a mediator

被引:51
作者
Hara, S [1 ]
Hatakeyama, T [1 ]
Chen, SQ [1 ]
Ishi-i, K [1 ]
Yoshida, M [1 ]
Sawaguchi, M [1 ]
Fukuhara, T [1 ]
Yoneda, N [1 ]
机构
[1] Hokkaido Univ, Grad Sch Engn, Div Mol Chem, Sapporo, Hokkaido 060, Japan
关键词
p-iodotoluene difluoride; alpha-fluoro-beta-dicarbonyl compounds; electrochemical fluorination;
D O I
10.1016/S0022-1139(97)00144-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The selective and direct introduction of the fluorine atom into the alpha-position of beta-dicarbonyl compounds was electrochemically achieved using iodotoluene difluoride as the mediator. The resulting alpha-fluoro-beta-dicarbonyl compounds are important building blocks for biologically active compounds. (C) 1998 Elsevier Science S.A.
引用
收藏
页码:189 / 192
页数:4
相关论文
共 29 条
[1]   N-HALOGENO COMPOUNDS .12. SITE-SPECIFIC FLUORINATION OF CARBANIONS WITH PERFLUORO-N-FLUOROPIPERIDINE [J].
BANKS, RE ;
MURTAGH, V ;
TSILIOPOULOS, E .
JOURNAL OF FLUORINE CHEMISTRY, 1991, 52 (03) :389-401
[2]   EFFICIENT ELECTROPHILIC FLUORINATION OF BETA-DICARBONYL COMPOUNDS WITH THE SELECTFLUOR REAGENT F-TEDA-BF4 (1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TETRAFLUOROBORATE)) [J].
BANKS, RE ;
LAWRENCE, NJ ;
POPPLEWELL, AL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) :343-344
[3]   ARYLIODOSODIFLUORIDES [J].
CARPENTER, W .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (08) :2688-+
[4]   DIRECT FLUORINATION OF 1,3-DICARBONYL COMPOUNDS [J].
CHAMBERS, RD ;
GREENHALL, MP ;
HUTCHINSON, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (01) :21-22
[5]   Elemental fluorine .2. Direct fluorination of 1,3-dicarbonyl compounds [J].
Chambers, RD ;
Greenhall, MP ;
Hutchinson, J .
TETRAHEDRON, 1996, 52 (01) :1-8
[6]   Electrochemical fluorination of aliphatic aldehydes and cyclic ketones using Et3N-5HF electrolyte [J].
Chen, SQ ;
HAtakeyama, T ;
Fukuhara, T ;
Hara, S ;
Yoneda, N .
ELECTROCHIMICA ACTA, 1997, 42 (13-14) :1951-1960
[8]   ELECTROCHEMICAL FLUORINATIVE ALPHA-CLEAVAGE OF CYCLIC-KETONES - SYNTHESIS OF FLUOROCARBOXYLIC ACID-ESTERS [J].
HARA, S ;
CHEN, SQ ;
HATAKEYAMA, T ;
FUKUHARA, T ;
SEKIGUCHI, M ;
YONEDA, N .
TETRAHEDRON LETTERS, 1995, 36 (36) :6511-6514
[9]   Electrochemically induced fluorinative ring expansion of cycloalkylideneacetates [J].
Hara, S ;
Chen, SQ ;
Hoshio, T ;
Fukuhara, T ;
Yoneda, N .
TETRAHEDRON LETTERS, 1996, 37 (47) :8511-8514
[10]  
HARA S, 1996, J CHEM SOC CHEM COMM, P1899