A highly efficient three-component coupling of aldehyde, alkyne, and amines via C-H activation catalyzed by gold in water

被引:643
作者
Wei, CM
Li, CJ [1 ]
机构
[1] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA
[2] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
关键词
D O I
10.1021/ja0359299
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly efficient three-component-coupling of aldehyde, alkyne, and amine (A3 Coupling) catalyzed by gold via C-H activation was developed in water. The reaction is general, and nearly quantitative yields of the corresponding propargylamines were obtained in most cases. Both aromatic and aliphatic aldehydes and amines can be used for the reaction. No additional cocatalyst or activator is required. A mechanistic rationale for the reaction has been proposed. Copyright © 2003 American Chemical Society.
引用
收藏
页码:9584 / 9585
页数:2
相关论文
共 46 条
  • [1] Anastas P. T., 1998, GREEN CHEM THEORY PR
  • [2] AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes
    Asao, N
    Takahashi, K
    Lee, S
    Kasahara, T
    Yamamoto, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) : 12650 - 12651
  • [3] Silver catalyzed zinc Barbier reaction of benzylic halides in water
    Bieber, LW
    Storch, EC
    Malvestiti, I
    da Silva, MF
    [J]. TETRAHEDRON LETTERS, 1998, 39 (51) : 9393 - 9396
  • [4] CHAN CJ, 1998, ORGANIC SYNTHESIS WA
  • [5] CROSSED ALDOL TYPE CONDENSATION-REACTIONS IN AQUEOUS-MEDIA
    CHAN, TH
    LI, CJ
    WEI, ZY
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (06) : 505 - 507
  • [6] Organometallic-type reactions in aqueous media mediated by indium: Application to the synthesis of carbohydrates
    Chan, TH
    Isaac, MB
    [J]. PURE AND APPLIED CHEMISTRY, 1996, 68 (04) : 919 - 924
  • [7] Zn(ODf)2:: preparation and application in asymmetric alkynylation of aldehydes
    Chen, ZL
    Xiong, WN
    Jiang, B
    [J]. CHEMICAL COMMUNICATIONS, 2002, (18) : 2098 - 2099
  • [8] Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO
  • [9] 2-6
  • [10] The discovery of novel reactivity in the development of C-C bond-forming reactions:: In situ generation of zinc acetylides with ZnII/R3N
    Frantz, DE
    Fässler, R
    Tomooka, CS
    Carreira, EM
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 373 - 381