BIMETALLIC CATALYSIS - SYNTHESIS OF BENZOPHENONES THROUGH CARBONYLATION OF ARYL IODIDES CATALYZED BY FE(CO)5-CO2(CO)8 SYSTEMS

被引:40
作者
BRUNET, JJ
TAILLEFER, M
机构
[1] Laboratoire de Chimie de Coordination, CNRS Unité no 8241 liée par conventions à l'Université Paul Sabatier, à l'Institut National Polytechnique, 31077 Toulouse Cedex
关键词
D O I
10.1016/0022-328X(90)87066-M
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The direct, catalytic carbonylation of aryl iodides to give the corresponding benzophenones is reported for the first time. Under phase transfer conditions (aq. NaOH/C6H6/Bu4NBr) and under 1 atm pressure of carbon monoxide, iron pentacarbonyl alone promotes the conversion of iodobenzene to benzophenone and benzoic acid, whereas dicobaltoctacarbonyl alone promotes a slow carbonylation to give solely benzoic acid. A synergetic effect is observed when the reaction is carried out in the presence of catalytic amounts of both carbonyl metals, and benzophenone can be isolated in more than 50% yield. Under these conditions, o-iodotoluene affords the corresponding 2,2′-dimethylbenzophenone in 47% isolated yield. © 1990.
引用
收藏
页码:193 / 197
页数:5
相关论文
共 33 条
[1]   NICKEL CYANIDE AND PHASE-TRANSFER-CATALYZED CARBONYLATION OF ARYL IODIDES IN THE ABSENCE OF LIGHT [J].
AMER, I ;
ALPER, H .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5147-5148
[2]   A FACILE, ONE-STEP, STEREOSELECTIVE SYNTHESIS OF NORBORNANE-2-CARBOXALDEHYDE [J].
BRUNET, JJ ;
KINDELA, FB ;
NEIBECKER, D .
SYNTHETIC COMMUNICATIONS, 1989, 19 (11-12) :1923-1928
[3]   SELECTIVE, IRON PENTACARBONYL CATALYZED REDUCTION OF ARYL IODIDES UNDER MILD CONDITIONS [J].
BRUNET, JJ ;
TAILLEFER, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 348 (01) :C5-C8
[4]   BIMETALLIC CATALYSIS - A NEW METHOD FOR CARBONYLATION OF ARYL IODIDES UNDER MILD CONDITIONS [J].
BRUNET, JJ ;
TAILLEFER, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 361 (01) :C1-C4
[5]   COBALT CARBONYL CATALYZED SRN1 CARBONYLATION OF ARYL AND VINYL HALIDES BY PHASE-TRANSFER CATALYSIS [J].
BRUNET, JJ ;
SIDOT, C ;
CAUBERE, P .
TETRAHEDRON LETTERS, 1981, 22 (11) :1013-1016
[6]   THE REACTION OF POTASSIUM TETRACARBONYLHYDRIDOFERRATE WITH ETHYL ACRYLATE IN ETHANOL [J].
BRUNET, JJ ;
PASSELAIGUE, E .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 375 (02) :203-215
[7]   ACTIVATION OF REDUCING AGENTS - SODIUM HYDRIDE CONTAINING COMPLEX REDUCING AGENTS .10. NAH-RONA-CO(OAC)2-CO, A NEW REAGENT FOR THE CARBONYLATION OF ARYL HALIDES AT ATMOSPHERIC-PRESSURE [J].
BRUNET, JJ ;
SIDOT, C ;
LOUBINOUX, B ;
CAUBERE, P .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) :2199-2202
[8]   EXPEDIENT SYNTHESIS OF (PH3P)2FE(CO)3 [J].
BRUNET, JJ ;
KINDELA, FB ;
NEIBECKER, D .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 368 (02) :209-212
[9]   SUNLAMP-IRRADIATED PHASE-TRANSFER CATALYSIS .1. COBALT CARBONYL CATALYZED SRN1 CARBONYLATIONS OF ARYL AND VINYL HALIDES [J].
BRUNET, JJ ;
SIDOT, C ;
CAUBERE, P .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (08) :1166-1171
[10]   PALLADIUM-CATALYZED CARBONYLATION OF ARYL IODIDES IN AQUEOUS-MEDIA [J].
BUMAGIN, NA ;
NIKITIN, KV ;
BELETSKAYA, IP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 358 (1-3) :563-565