Copper-catalyzed Markovnikov hydration of alkynes

被引：45
作者：
Hassam, Mohammad [1 ]
Li, Wen-Shan [1 ,2 ]
机构：
[1] Acad Sinica, Inst Chem, Taipei 115, Taiwan
[2] Natl Sun Yat Sen Univ, Doctoral Degree Program Marine Biotechnol, Kaohsiung 804, Taiwan
来源：
TETRAHEDRON | 2015年 / 71卷 / 18期
关键词：
Alkynes; Copper triflate; Hydration; Ethyl acetate; ACID; COMPLEXES; DERIVATIVES; PALLADIUM; ALCOHOLS;
D O I：
10.1016/j.tet.2015.03.034
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Conventional, highly efficient, inexpensive copper trifiate catalyzed regioselective Markovnikov hydration of terminal and internal alkynes have been reported. Significant shorter reaction time and excellent yield without addition of additive make the method attractive. Effects of catalyst and solvent on the hydration reaction have also been studied. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2719 / 2723
页数：5
相关论文
共 31 条
  • [1] Mixed Phosphane η5-CpRuCl(PR3)2 Complexes as Ambifunctional Catalysts for Anti-Markovnikov Hydration of Terminal Alkynes
    Boeck, Florian
    Kribber, Thomas
    Xiao, Li
    Hintermann, Lukas
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) : 8138 - 8141
  • [2] HOMOGENEOUSLY CATALYZED HYDRATION OF ACETYLENES BY MERCURIC PERCHLORATE-PERCHLORIC ACID - EVIDENCE FOR A BIS-(ACETYLENE)-MERCURIC ION COMPLEX AS AN INTERMEDIATE
    BUDDE, WL
    DESSY, RE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (24) : 3964 - &
  • [3] Regioselective Hydration of Alkynes by Iron(III) Lewis/Bronsted Catalysis
    Cabrero-Antonino, Jose R.
    Leyva-Perez, Antonio
    Corma, Avelino
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (35) : 11107 - 11114
  • [4] Isomerization of propargylic alcohols into α,β-unsaturated carbonyl compounds catalyzed by the sixteen-electron allyl-ruthenium(II) complex [Ru(η3-2-C3H4Me)(CO)(dppf)] [SbF6]
    Cadierno, V
    García-Garrido, SE
    Gimeno, J
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) : 101 - 110
  • [5] Highly efficient AgBF4-catalyzed synthesis of methyl ketones from terminal alkynes
    Chen, Zheng-Wang
    Ye, Dong-Nai
    Qian, Yi-Ping
    Ye, Min
    Liu, Liang-Xian
    [J]. TETRAHEDRON, 2013, 69 (30) : 6116 - 6120
  • [6] AgOTf catalyzed hydration of terminal alkynes
    Das, Rima
    Chakraborty, Debashis
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2012, 26 (12) : 722 - 726
  • [7] Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis
    Gawande, Manoj B.
    Bonifacio, Vasco D. B.
    Luque, Rafael
    Branco, Paula S.
    Varma, Rajender S.
    [J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) : 5522 - 5551
  • [8] p-Toluenesulfonic acid-promoted selective functionalization of unsymmetrical arylalkynes: a regioselective access to various arylketones and heterocycles
    Jacubert, Maud
    Provot, Olivier
    Peyrat, Jean-Francois
    Hamze, Abdallah
    Brion, Jean-Daniel
    Alami, Mouad
    [J]. TETRAHEDRON, 2010, 66 (21) : 3775 - 3787
  • [9] Microwave assisted copper triflate-catalyzed rapid hydration of aryl acetylenes
    Jha, Mukund
    Shelke, Ganesh M.
    Pericherla, Kasiviswanadharaju
    Kumar, Anil
    [J]. TETRAHEDRON LETTERS, 2014, 55 (34) : 4814 - 4816
  • [10] Isolation and Crystal Structures of Both Enol and Keto Tautomer Intermediates in a Hydration of an Alkyne-Carboxylic Acid Ester Catalyzed by Iridium Complexes in Water
    Kanemitsu, Hironobu
    Uehara, Keiji
    Fukuzumi, Shunichi
    Ogo, Seiji
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (50) : 17141 - 17147
1234