Development of new palladium catalysts for the alkoxycarbonylation of aryl chlorides

被引:84
作者
Mägerlein, W
Indolese, AF
Beller, M
机构
[1] Univ Rostock EV, Inst Organ Katalyseforschung IfOK, D-18055 Rostock, Germany
[2] Solvias AG, CH-4002 Basel, Switzerland
关键词
carbonylation; palladium; ferrocenyl phosphines; aryl chlorides; homogeneous catalysis; benzoic acids;
D O I
10.1016/S0022-328X(01)01293-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The alkoxycarbonylation of different aryl chlorides was studied. Studies of the butoxycarbonylation of 4-chlorobenzotrifluoride and chlorobenzene using chelating ferrocenylphosphines reveal the advantages of these ligands compared to the wen-known tricyclohexylphosphine (PCy3). (1-(2-(Dicyclohexylphosphino)ferroceuyl)ethyldicyclohexylphosphine (4) was shown to give the most active palladium catalyst system. The usefulness of this catalyst is demonstrated in the alkoxycarbonylation of various aryl chlorides. Optimized carbonylation conditions were realized by a statistical design of three critical reaction parameters. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:30 / 40
页数:11
相关论文
共 65 条
[41]   A highly active catalyst for palladium-catalyzed cross-coupling reactions: Room-temperature Suzuki couplings and amination of unactivated aryl chlorides [J].
Old, DW ;
Wolfe, JP ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (37) :9722-9723
[42]   Palladium-catalyzed carbonylation and coupling reactions of aryl chlorides and amines [J].
Perry, RJ ;
Wilson, BD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7482-7485
[43]   MECHANISM OF ARYL CHLORIDE OXIDATIVE ADDITION TO CHELATED PALLADIUM(0) COMPLEXES [J].
PORTNOY, M ;
MILSTEIN, D .
ORGANOMETALLICS, 1993, 12 (05) :1665-1673
[44]   CHELATE EFFECT ON THE STRUCTURE AND REACTIVITY OF ELECTRON-RICH PALLADIUM COMPLEXES AND ITS RELEVANCE TO CATALYSIS [J].
PORTNOY, M ;
MILSTEIN, D .
ORGANOMETALLICS, 1993, 12 (05) :1655-1664
[45]  
Reetz MT, 1998, ANGEW CHEM INT EDIT, V37, P481, DOI 10.1002/(SICI)1521-3773(19980302)37:4<481::AID-ANIE481>3.0.CO
[46]  
2-I
[47]   Palladium-catalyzed C-C- and C-N-coupling reactions of aryl chlorides [J].
Riermeier, TH ;
Zapf, A ;
Beller, M .
TOPICS IN CATALYSIS, 1997, 4 (3-4) :301-309
[48]   PALLADIUM-CATALYZED CARBOALKOXYLATION OF ARYL, BENZYL, AND VINYLIC HALIDES [J].
SCHOENBE.A ;
BARTOLET.I ;
HECK, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (23) :3318-3326
[49]   A fluorescence-based assay for high-throughput screening of coupling reactions. Application to Heck chemistry [J].
Shaughnessy, KH ;
Kim, P ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (10) :2123-2132
[50]  
Spindler F, 1999, ENANTIOMER, V4, P557