Selective NaOH-catalysed hydration of aromatic nitriles to amides

被引:24
作者
Schmid, Thibault E. [1 ]
Gomez-Herrera, Alberto [1 ]
Songis, Olivier [1 ]
Sneddon, Deborah [1 ]
Revolte, Antoine [1 ]
Nahra, Fady [1 ]
Cazin, Catherine S. J. [1 ]
机构
[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland
关键词
COMPLEXES; ACID; HYDROLYSIS; CONVERSION; EFFICIENT; WATER; MECHANISM; ORGANONITRILES; PALLADIUM(II); ACTIVATION;
D O I
10.1039/c5cy00313j
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
The selective synthesis of aromatic and heteroaromatic amides through base-catalysed hydration of nitriles was achieved using inexpensive and commercially available NaOH as the only catalyst. A wide range of nitriles was selectively converted to their corresponding amides. Kinetic studies show that the double hydration of nitriles towards undesirable carboxylic acids is negligible under our reaction conditions.
引用
收藏
页码:2865 / 2868
页数:4
相关论文
共 47 条
[1]  
[Anonymous], THE CHEMISTRY OF AMI
[2]   Mild and Selective Heterogeneous Catalytic Hydration of Nitriles to Amides by Flowing through Manganese Dioxide [J].
Battilocchio, Claudio ;
Hawkins, Joel M. ;
Ley, Steven V. .
ORGANIC LETTERS, 2014, 16 (04) :1060-1063
[3]   Efficient and selective nitrile hydration reactions in water catalyzed by an unexpected dimethylsulfinyl anion generated in situ from CsOH and DMSO [J].
Chen, Haonan ;
Dai, Wujie ;
Chen, Yi ;
Xu, Qing ;
Chen, Jianhui ;
Yu, Lei ;
Zhao, Yajuan ;
Ye, Mingde ;
Pan, Yuanjiang .
GREEN CHEMISTRY, 2014, 16 (04) :2136-2141
[4]   Bifunctional Water Activation for Catalytic Hydration of Organonitriles [J].
Daw, Prosenjit ;
Sinha, Arup ;
Rahaman, S. M. Wahidur ;
Dinda, Shrabani ;
Bera, Jitendra K. .
ORGANOMETALLICS, 2012, 31 (09) :3790-3797
[5]  
Deopura BL, 2008, WOODHEAD PUBL TEXT, P41, DOI 10.1533/9781845694609.1.41
[6]   Ru(II) complexes containing dmso and pyrazolyl ligands as catalysts for nitrile hydration in environmentally friendly media [J].
Ferrer, Ingrid ;
Rich, Jordi ;
Fontrodona, Xavier ;
Rodriguez, Montserrat ;
Romero, Isabel .
DALTON TRANSACTIONS, 2013, 42 (37) :13461-13469
[7]   Metal-catalyzed amide bond forming reactions in an environmentally friendly aqueous medium: nitrile hydrations and beyond [J].
Garcia-Alvarez, Rocio ;
Crochet, Pascale ;
Cadierno, Victorio .
GREEN CHEMISTRY, 2013, 15 (01) :46-66
[8]   Arene-Ruthenium(II) Complexes Containing Amino-Phosphine Ligands as Catalysts for Nitrite Hydration Reactions [J].
Garcia-Alvarez, Rocio ;
Diez, Josefina ;
Crochet, Pascale ;
Cadierno, Victorio .
ORGANOMETALLICS, 2010, 29 (17) :3955-3965
[9]   Catalytic applications of a versatile magnetically separable Fe-Mo (Nanocat-Fe-Mo) nanocatalyst [J].
Gawande, Manoj B. ;
Branco, Paula S. ;
Nogueira, Isabel D. ;
Ghumman, C. Amjad A. ;
Bundaleski, Nenad ;
Santos, Aderito ;
Teodoro, Orlando M. N. D. ;
Luque, Rafael .
GREEN CHEMISTRY, 2013, 15 (03) :682-689
[10]   The catalytic hydration of nitriles to amides using a homogeneous platinum phosphinito catalyst [J].
Ghaffar, T ;
Parkins, AW .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 160 (02) :249-261