Palladium-catalyzed cross-coupling reactions in total synthesis

被引:2455
作者
Nicolaou, KC
Bulger, PG
Sarlah, D
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[3] Univ Calif San Diego, Dept Biochem & Chem, La Jolla, CA 92093 USA
关键词
C-C coupling; cross-coupling; palladium catalysis; synthetic methods; total synthesis;
D O I
10.1002/anie.200500368
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) In studying the evolution of organic chemistry and grasping its essence, one comes quickly to the conclusion that no other type of reaction plays as large a role in shaping this domain of science than carbon-carbon bond-forming reactions. The Grignard, Diels-Alder, and Wittig reactions are but three prominent examples of such processes, and are among those which have undeniably exercised decisive roles in the last century in the emergence of chemical synthesis as we know it today. In the last quarter of the 20th century, a new family of carbon-carbon bond-forming reactions based on transition-metal catalysts evolved as powerful tools in synthesis. Among them, the palladium-catalyzed cross-coupling reactions are the most prominent. In this Review, high-lights of a number of selected syntheses are discussed. The examples chosen demonstrate the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4442 / 4489
页数:48
相关论文
共 518 条
  • [21] Total synthesis and structural elucidation of the antifungal agent papulacandin D
    Barrett, AGM
    Pena, M
    Willardsen, JA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) : 1082 - 1100
  • [22] Synthetic studies toward SNF4435 C and SNF4435 D
    Beaudry, CM
    Trauner, D
    [J]. ORGANIC LETTERS, 2002, 4 (13) : 2221 - 2224
  • [23] The enantioselective Tsuji allylation
    Behenna, DC
    Stoltz, BM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) : 15044 - 15045
  • [24] The heck reaction as a sharpening stone of palladium catalysis
    Beletskaya, IP
    Cheprakov, AV
    [J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
  • [25] 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
  • [26] Beller M., 1995, ANGEW CHEM, V107, P1992
  • [27] Bodwell GJ, 2002, ANGEW CHEM INT EDIT, V41, P3261, DOI 10.1002/1521-3773(20020902)41:17<3261::AID-ANIE3261>3.0.CO
  • [28] 2-K
  • [29] Diastereoselective total synthesis of the vancomycin aglycon with ordered atropisomer equilibrations
    Boger, DL
    Miyazaki, S
    Kim, SH
    Wu, JH
    Loiseleur, O
    Castle, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) : 3226 - 3227
  • [30] STUDIES ON THE SYNTHESIS OF STRYCHNOS INDOLE ALKALOIDS - SYNTHESIS OF (+/-)-DEHYDROTUBIFOLINE
    BONJOCH, J
    SOLE, D
    BOSCH, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) : 11017 - 11018