Efficient and selective hydration of nitriles to amides in aqueous systems with Ru(II)-phosphaurotropine catalysts

被引：39
作者：
Bolyog-Nagy, Evelin [1 ]
Udvardy, Antal [1 ]
Joo, Ferenc [1 ,2 ]
Katho, Agnes [1 ]
机构：
[1] Univ Debrecen, Dept Phys Chem, H-4032 Debrecen, Hungary
[2] MTA DE, Homogeneous Catalysis & React Mech Res Grp, H-4032 Debrecen, Hungary
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 26期
关键词：
Nitrile hydration; Ruthenium; Phosphine; Amides; ARENE-RUTHENIUM(II) COMPLEXES; RUTHENIUM(II) COMPLEXES; WATER; LIGANDS; 1,3,5-TRIAZA-7-PHOSPHAADAMANTANE; ORGANONITRILES; BOND;
D O I：
10.1016/j.tetlet.2014.04.118
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient synthesis of amides by selective hydration of aromatic and aliphatic nitriles is described. The catalysts are prepared in situ from easily available Ru-precursors and ligands using water as the solvent. The most active catalyst, is obtained from [RuCl2(dmso)(4)] and benzylated 1,3,5-triaza-7-phosphaadamantane. Of the 16 substrates examined, 92-99% conversions of 14 nitriles were achieved in one hour at reflux temperature. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3615 / 3617
页数：3
相关论文
共 32 条
  • [1] Frontiers in catalytic nitrile hydration: Nitrile and cyanohydrin hydration catalyzed by homogeneous organometallic complexes
    Ahmed, Takiya J.
    Knapp, Spring Melody M.
    Tyler, David R.
    [J]. COORDINATION CHEMISTRY REVIEWS, 2011, 255 (7-8) : 949 - 974
  • [2] THE RELATIVE AFFINITIES OF CO-ORDINATING ATOMS FOR SILVER ION .1. OXYGEN, SULPHUR, AND SELENIUM
    AHRLAND, S
    CHATT, J
    DAVIES, NR
    WILLIAMS, AA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1958, (JAN): : 264 - 276
  • [3] ARENE RUTHENIUM(II) COMPLEXES FORMED BY DEHYDROGENATION OF CYCLOHEXADIENES WITH RUTHENIUM(III) TRICHLORIDE
    BENNETT, MA
    SMITH, AK
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (02): : 233 - 241
  • [4] Selective ruthenium-catalyzed hydration of nitriles to amides in pure aqueous medium under neutral conditions
    Cadierno, Victorio
    Francos, Javier
    Gimeno, Jose
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (22) : 6601 - 6605
  • [5] Bis(allyl)ruthenium(IV) Complexes Containing Water-Soluble Phosphane Ligands: Synthesis, Structure, and Application as Catalysts in the Selective Hydration of Organonitriles into Amides
    Cadierno, Victorio
    Diez, Josefina
    Francos, Javier
    Gimeno, Jose
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (32) : 9808 - 9817
  • [6] 1,3,5-TRIAZA-7-PHOSPHATRICYCLO[3.3.1.13,7]DECANE AND DERIVATIVES
    Daigle, DJ
    Decuir, TJ
    Robertson, JB
    Darensbourg, DJ
    [J]. INORGANIC SYNTHESES, VOL 32, 1998, 32 : 40 - 45
  • [7] SYNTHESIS OF A MONOPHOSPHORUS ANALOG OF HEXAMETHYLENETETRAMINE
    DAIGLE, DJ
    PEPPERMA.AB
    VAIL, SL
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1974, 11 (03) : 407 - 408
  • [8] A new water-soluble phosphine derived from 1,3,5-triaza-7-phosphaadamantane (PTA), 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane. Structural, bonding, and solubility properties
    Darensbourg, DJ
    Ortiz, CG
    Kamplain, JW
    [J]. ORGANOMETALLICS, 2004, 23 (08) : 1747 - 1754
  • [9] The hydration of nitriles catalyzed by water-soluble rhodium complexes
    Djoman, MCKB
    Ajjou, AN
    [J]. TETRAHEDRON LETTERS, 2000, 41 (25) : 4845 - 4849
  • [10] DICHLOROTETRAKIS(DIMETHYL SULPHOXIDE)RUTHENIUM(II) AND ITS USE AS A SOURCE MATERIAL FOR SOME NEW RUTHENIUM(II) COMPLEXES
    EVANS, IP
    SPENCER, A
    WILKINSO.G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1973, (02): : 204 - 209
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