Pd-Catalyzed Three-Component Coupling of N-Tosylhydrazone, Terminal Alkyne, and Aryl Halide

被引：184
作者：
Zhou, Lei [1 ]
Ye, Fei [1 ]
Zhang, Yan [1 ]
Wang, Jianbo [1 ]
机构：
[1] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Coll Chem, Minist Educ,BNLMS, Beijing 100871, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 39期
基金：
中国博士后科学基金;
关键词：
CARBENE INSERTION; VINYL HALIDES; DIAZOESTERS; REAGENTS; BROMIDES;
D O I：
10.1021/ja105762n
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A Pd-catalyzed three-component reaction of N-tosylhydrazone, terminal alkyne, and aryl halide follows a mechanism involving a sequence of Pd carbene migratory insertion-trans-metalation reductive elimination, leading to the formation of one sp(2)-sp(3) C-C bond and one sp-sp(3) C-C bond.
引用
收藏
页码：13590 / 13591
页数：2
相关论文
共 28 条
  • [1] The first palladium-catalyzed Sonogashira coupling of unactivated secondary alkyl bromides
    Altenhoff, G
    Würtz, S
    Glorius, F
    [J]. TETRAHEDRON LETTERS, 2006, 47 (17) : 2925 - 2928
  • [2] Pd-catalyzed cross-coupling reactions with carbonyls:: Application in a very efficient synthesis of 4-aryltetrahydropyridines
    Barluenga, Jose
    Tomas-Gamasa, Maria
    Moriel, Patricia
    Amar, Fernando
    Valdes, Carlos
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) : 4792 - 4795
  • [3] N-tosylhydrazones as reagents for cross-coupling reactions:: A route to polysubstituted olefins
    Barluenga, José
    Moriel, Patricia
    Valdes, Carlos
    Aznar, Fernando
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) : 5587 - 5590
  • [4] Synthesis of Enol Ethers and Enamines by Pd-Catalyzed Tosylhydrazide-Promoted Cross-Coupling Reactions
    Barluenga, Jose
    Escribano, Maria
    Moriel, Patricia
    Aznar, Fernando
    Valdes, Carlos
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (48) : 13291 - 13294
  • [5] Enantioselective nickel-catalyzed cross-coupling reactions of trialkynylindium reagents with racemic secondary benzyl bromides
    Caeiro, Jorge
    Sestelo, Jose Perez
    Sarandeses, Luis A.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (02) : 741 - 746
  • [6] Palladium-catalyzed reaction of allyl halides with α-diazocarbonyl compounds
    Chen, Shufeng
    Wang, Jianbo
    [J]. CHEMICAL COMMUNICATIONS, 2008, (35) : 4198 - 4200
  • [7] Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion
    Davies, HML
    Beckwith, REJ
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2861 - 2903
  • [8] Palladium-catalyzed carbene insertion and trapping with carbon nucleophiles
    Devine, Sean K. J.
    Van Vranken, David L.
    [J]. ORGANIC LETTERS, 2008, 10 (10) : 1909 - 1911
  • [9] Palladium-catalyzed carbene insertion into vinyl halides and trapping with amines
    Devine, Sean K. J.
    Van Vranken, David L.
    [J]. ORGANIC LETTERS, 2007, 9 (10) : 2047 - 2049
  • [10] Doyle M. P., 1998, MODERN CATALYTIC MET
123