Selective ruthenium-catalyzed hydration of nitriles to amides in pure aqueous medium under neutral conditions

被引:161
作者
Cadierno, Victorio [1 ]
Francos, Javier [1 ]
Gimeno, Jose [1 ]
机构
[1] Univ Oviedo, CSIC, Unidad Asociada,Dept Quim Organ & Inrogan, Inst Univ Quim Organomet Enrique Moles, Oviedo 33006, Spain
关键词
amides; homogeneous catalysis; hydration; nitriles; ruthenium;
D O I
10.1002/chem.200800847
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A study was conducted to demonstrate that water-soluble ruthenium(II) complexes can be used as catalysts for the hydration of nitriles in pure aqueous media and under neutral conditions. The hydration of benzonitrile was investigated as a model reaction and the ruthenium precursor was added to a 0.33M aqueous solution of benzonitrile at 100°C, while the reaction was monitored by gas chromatography. All the complexes checked, were found to be active and selective catalysts in the hydration process, providing benzamide as a specific reaction product. The most relevant results were obtained by using ruthenium complexes, bearing a nitrogen-containing ligand, which led to appropriate production of benzamide. The most effective ruthenium complex was found to be an efficient catalyst for the selective hydration of a large number of other nitriles.
引用
收藏
页码:6601 / 6605
页数:5
相关论文
共 56 条
[11]   Bis(allyl)-ruthenium(IV) complexes as highly efficient catalysts for the redox isomerization of allylic alcohols into carbonyl compounds in organic and aqueous media:: Scope, limitations, and theoretical analysis of the mechanism [J].
Cadierno, V ;
García-Garrido, SE ;
Gimeno, J ;
Varela-Alvarez, A ;
Sordo, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1360-1370
[12]   Ru(IV)-catalyzed isomerization of allylamines in water:: A highly efficient procedure for the deprotection of N-allylic amines [J].
Cadierno, V ;
García-Garrido, SE ;
Gimeno, J ;
Nebra, N .
CHEMICAL COMMUNICATIONS, 2005, (32) :4086-4088
[13]   Water-soluble ruthenium(II) catalysts [RuCl2(η6-arene)-{P(CH2OH)3}] for isomerization of allylic alcohols and alkyne hydration [J].
Cadierno, V ;
Crochet, P ;
García-Garrido, SE ;
Gimeno, J .
DALTON TRANSACTIONS, 2004, (21) :3635-3641
[14]   Dichloro(dodeca-2,6,10-triene-1,12-diyl)ruthenium(IV):: a highly efficient catalyst for the isomerization of allylic alcohols into carbonyl compounds in organic and aqueous media [J].
Cadierno, V ;
García-Garrido, SE ;
Gimeno, J .
CHEMICAL COMMUNICATIONS, 2004, (02) :232-233
[15]   Efficient tandem process for the catalytic deprotection of N-allyl amides and lactams in aqueous media:: A novel application of the bis(allyl)ruthenium(IV) catalysts [Ru(η3:η2:η3-C12H18)Cl2] and [{Ru(η3:η3-C10H16)-(μ-Cl)Cl}2] [J].
Cadierno, Victorio ;
Gimeno, Jose ;
Nebra, Noel .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (23) :6590-6594
[16]   Ruthenium-catalyzed reduction of allylic alcohols: An efficient isomerization/transfer hydrogenation tandem process [J].
Cadierno, Victorio ;
Francos, Javier ;
Gimeno, Jose ;
Nebra, Noel .
CHEMICAL COMMUNICATIONS, 2007, (24) :2536-2538
[17]   Efficient intermolecular [2+2+2] alkyne cyclotrimerization in aqueous medium using a ruthenium(IV) precatalyst [J].
Cadierno, Victorio ;
Garcia-Garrido, Sergio E. ;
Gimeno, Jose .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (47) :15094-15095
[18]  
Chin CS, 1999, B KOREAN CHEM SOC, V20, P535
[19]  
Cornils B., 2006, Aqueous -Phase Organometallic Catalysis: Concepts and Applications
[20]   Catalytic hydration of benzonitrile and acetonitrile using nickel(0) [J].
Crestani, MG ;
Arévalo, A ;
García, JJ .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (06) :732-742