Regioselective (site-selective) functionalisation of unsaturated halogenated nitrogen, oxygen and sulfur heterocycles by Pd-catalysed cross-couplings and direct arylation processes

被引:362
作者
Fairlamb, Ian J. S. [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
关键词
D O I
10.1039/b611177g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This tutorial review focuses on several practical synthetic transformations utilising palladium catalysis that facilitate the synthesis of functionalised unsaturated heterocycles in a regioselective ( site-selective) manner. Cross-couplings of electron-deficient, electron-neutral and electron-rich unsaturated halogenated heterocycles with various organometallic reagents, and other types of nucleophiles, are detailed. Direct arylation of electron-rich unsaturated heterocyclic compounds by C - H functionalisation is also presented.
引用
收藏
页码:1036 / 1045
页数:10
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共 61 条
  • [1] Role of dba in the reactivity of palladium(0) complexes generated in situ from mixtures of Pd(dba)2 and phosphines
    Amatore, C
    Jutand, A
    [J]. COORDINATION CHEMISTRY REVIEWS, 1998, 178 : 511 - 528
  • [2] A new precatalyst for the Suzuki reaction -: a pyridyl-bridged dinuclear palladium complex as a source of mono-ligated palladium(0)
    Beeby, A
    Bettington, S
    Fairlamb, IJS
    Goeta, AE
    Kapdi, AR
    Niemelä, EH
    Thompson, AL
    [J]. NEW JOURNAL OF CHEMISTRY, 2004, 28 (05) : 600 - 605
  • [3] Palladium- and copper-mediated direct C-2 arylation of azoles - Including free (NH)-imidazole, -benzimidazole and -indole - Under base-free and ligandless conditions
    Bellina, F
    Cauteruccio, S
    Rossi, R
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (06) : 1379 - 1382
  • [4] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules
    Campeau, LC
    Fagnou, K
    [J]. CHEMICAL COMMUNICATIONS, 2006, (12) : 1253 - 1264
  • [5] Analysis of the reactions used for the preparation of drug candidate molecules
    Carey, John S.
    Laffan, David
    Thomson, Colin
    Williams, Mike T.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) : 2337 - 2347
  • [6] Microwave-assisted, efficient and regioselective Pd-catalyzed C-phenylation of halopyrimidines
    Ceide, Susana Conde
    Montalban, Antonio Garrido
    [J]. TETRAHEDRON LETTERS, 2006, 47 (26) : 4415 - 4418
  • [7] Direct C-H arylation of purines:: Development of methodology and its use in regioselective synthesis of 2,6,8-trisubstituted purines
    Cerna, Igor
    Pohl, Radek
    Klepetarova, Blanka
    Hocek, Michal
    [J]. ORGANIC LETTERS, 2006, 8 (23) : 5389 - 5392
  • [8] Efficient synthesis of a trisubstituted 1,6-naphthyridone from acetonedicarboxylate and regioselective Suzuki arylation
    Chung, JYL
    Cai, CX
    McWilliams, JC
    Reamer, RA
    Dormer, PG
    Cvetovich, RJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (25) : 10342 - 10347
  • [9] CLAVIUS CHC, 1998, J CHEM SOC DA, P3777
  • [10] Palladium-catalyzed carbonylative coupling of pyridine halides with aryl boronic acids
    Couve-Bonnaire, S
    Carpentier, JF
    Mortreux, A
    Castanet, Y
    [J]. TETRAHEDRON, 2003, 59 (16) : 2793 - 2799