Cationic Gold Catalyzes ω-Bromination of Terminal Alkynes and Subsequent Hydroaddition Reactions

被引:33
作者
Leyva-Perez, Antonio [1 ]
Rubio-Marques, Paula [1 ]
Al-Deyab, Salem S. [2 ]
Al-Resayes, Saud I. [2 ]
Corma, Avelino [1 ,2 ]
机构
[1] Univ Politecn Valencia, Inst Tecnol Quim, Consejo Super Invest Cient, Valencia 46022, Spain
[2] King Saud Univ, Coll Sci, Dept Chem, Riyadh 11451, Saudi Arabia
来源
ACS CATALYSIS | 2011年 / 1卷 / 06期
关键词
gold catalysis; aurophilic interactions; terminal alkynes; sigma; pi-bisfunctionalization; bromoalkynes; BOND-FORMING REACTIONS; ONE-POT SYNTHESIS; INTERMOLECULAR HYDROAMINATION; ORGANOGOLD COMPOUNDS; ROOM-TEMPERATURE; LEWIS-ACID; COMPLEXES; ACTIVATION; ACETYLIDES; EFFICIENT;
D O I
10.1021/cs200168p
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
Orthogonal sigma,pi-bisfunctionalization of terminal alkynes can be achieved with a cationic gold complex in catalytic amounts. First, the terminal C-H bond is transformed to the corresponding bromoalkyne which is then activated toward nucleophilic attack. This reactivity correlates with the structural nature of isolated gold-alkyne complexes.
引用
收藏
页码:601 / 606
页数:6
相关论文
共 70 条
  • [1] Mechanistic Insights into the One-Pot Synthesis of Propargylamines from Terminal Alkynes and Amines in Chlorinated Solvents Catalyzed by Gold Compounds and Nanoparticles
    Aguilar, David
    Contel, Maria
    Urriolabeitia, Esteban P.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (30) : 9287 - 9296
  • [2] BASCH H, 2004, NATURE TRIPLE BOND T, P1
  • [3] BLAKE D, 1959, P CHEM SOC LONDON, P396
  • [4] Homoleptic transition metal acetylides
    Buschbeck, Roy
    Low, Paul J.
    Lang, Heinrich
    [J]. COORDINATION CHEMISTRY REVIEWS, 2011, 255 (1-2) : 241 - 272
  • [5] Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans
    Buzas, A
    Istrate, F
    Gagosz, F
    [J]. ORGANIC LETTERS, 2006, 8 (09) : 1957 - 1959
  • [6] Gold(I)-catalyzed formation of 4-alkylidene-1,3-dioxolan-2-ones from propargylic tert-butyl carbonates
    Buzas, A
    Gagosz, F
    [J]. ORGANIC LETTERS, 2006, 8 (03) : 515 - 518
  • [7] Gold-catalyzed rearrangement of propargylic tert-butyl carbonates
    Buzas, Andrea K.
    Istrate, Florin M.
    Gagosz, Fabien
    [J]. TETRAHEDRON, 2009, 65 (09) : 1889 - 1901
  • [8] Silver-Catalyzed Difunctionalization of Terminal Alkynes: Highly Regio- and Stereoselective Synthesis of (Z)-β-Haloenol Acetates
    Chen, Zhengwang
    Li, Jinghao
    Jiang, Huanfeng
    Zhu, Shifa
    Li, Yibiao
    Qi, Chaorong
    [J]. ORGANIC LETTERS, 2010, 12 (14) : 3262 - 3265
  • [9] Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction
    Cheong, Paul Ha-Yeon
    Morganelli, Philip
    Luzung, Michael R.
    Houk, K. N.
    Toste, F. Dean
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (13) : 4517 - 4526
  • [10] General and Efficient Copper-Catalyzed Three-Component Coupling Reaction towards Imidazoheterocycles: One-Pot Synthesis of Alpidem and Zolpidem
    Chernyak, Natalia
    Gevorgyan, Vladimir
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (15) : 2743 - 2746