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
  • [1] Molecularly defined palladium(0) monophosphine complexes as catalysts for efficient cross-coupling of aryl chlorides and phenylboronic acid
    Andreu, MG
    Zapf, A
    Beller, M
    [J]. CHEMICAL COMMUNICATIONS, 2000, (24) : 2475 - 2476
  • [2] [Anonymous], [No title captured], Patent No. 385210
  • [3] A convenient palladium/ligand catalyst for Suzuki cross-coupling reactions of arylboronic acids and aryl chlorides
    Bei, XH
    Crevier, T
    Guram, AS
    Jandeleit, B
    Powers, TS
    Turner, HW
    Uno, T
    Weinberg, WH
    [J]. TETRAHEDRON LETTERS, 1999, 40 (20) : 3855 - 3858
  • [4] Beller M, 2001, SYNTHESIS-STUTTGART, P1098, DOI 10.1055/s-2001-14576
  • [5] PROGRESS IN HYDROFORMYLATION AND CARBONYLATION
    BELLER, M
    CORNILS, B
    FROHNING, CD
    KOHLPAINTNER, CW
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 104 (01) : 17 - 85
  • [6] PALLADACYCLES AS EFFICIENT CATALYSTS FOR ARYL COUPLING REACTIONS
    BELLER, M
    FISCHER, H
    HERRMANN, WA
    OFELE, K
    BROSSMER, C
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17): : 1848 - 1849
  • [7] Beller M, 1998, SYNLETT, P792
  • [8] BELLER M, 1996, APPL HOMOGENEOUS CAT, V2, P148
  • [9] BELLER M, 1998, TRANSITION METALS OR
  • [10] CHELATE-ASSISTED, PD-CATALYZED EFFICIENT CARBONYLATION OF ARYL CHLORIDES
    BENDAVID, Y
    PORTNOY, M
    MILSTEIN, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) : 8742 - 8744