Comparison of palladium carbene and palladium phosphine catalysts for catalytic coupling reactions of aryl halides

被引:75
作者
Frisch, AC
Zapf, A
Briel, O
Kayser, B
Shaikh, N
Beller, M
机构
[1] Univ Rostock eV, Leibniz Inst Organ Katalyse, D-18055 Rostock, Germany
[2] Umicore AG&Co KG, D-63403 Hanau, Germany
关键词
aryl halides; carbene ligands; homogeneous catalysis; palladium; phosphine ligands;
D O I
10.1016/j.molcata.2003.12.035
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Palladium-catalyzed C-C and C-N bond forming reactions of aryl halides continue to be a major focus in catalysis research for the fine chemical industry. Still there exists a significant need for the development of more active and productive palladium catalysts. Although an increasing number of new catalysts is reported, it is often difficult to compare them. Here, we present a more detailed comparison of the catalytic performance of different monocarbenepalladium(0) complexes and various so-called in situ palladium phosphine and carbene catalysts in Suzuki, Kumada, and Buchwald-Hartwig animation reactions. Depending on the type of coupling reaction good to excellent yields of the desired products are obtained in the presence of both carbene- and phosphine-based catalysts. In general, phosphine-based catalysts appear to be more efficient for amination and Suzuki reactions of aryl chlorides. On the other hand, the carbene-based palladium catalysts work well in Kumada couplings of various aryl chlorides. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:231 / 239
页数:9
相关论文
共 92 条
  • [1] An improved method for the palladium-catalyzed amination of aryl iodides
    Ali, MH
    Buchwald, SL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) : 2560 - 2565
  • [2] Anastasia L., 2002, ORGANOPALLADIUM CHEM, V1, P311
  • [3] 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
  • [4] [Anonymous], 2002, ANGEW CHE
  • [5] [Anonymous], 2013, ANGEW CHEM, V125, P4315, DOI DOI 10.1002/1521-3757(20001117)112:22
  • [6] [Anonymous], ANGEW CHEM
  • [7] [Anonymous], ANGEW CHEM
  • [8] Bedford RB, 2002, ANGEW CHEM INT EDIT, V41, P4120, DOI 10.1002/1521-3773(20021104)41:21<4120::AID-ANIE4120>3.0.CO
  • [9] 2-7
  • [10] Palladium bis(phosphinite) 'PCP'-pincer complexes and their application as catalysts in the Suzuki reaction
    Bedford, RB
    Draper, SM
    Scully, PN
    Welch, SL
    [J]. NEW JOURNAL OF CHEMISTRY, 2000, 24 (10) : 745 - 747