A supported rhodium hydroxide catalyst: Preparation, characterization, and scope of the synthesis of primary amides from aldoximes or aldehydes

被引:74
作者
Fujiwara, Hiroshi [1 ]
Ogasawara, Yoshiyuki [1 ]
Kotani, Miyuki [2 ]
Yamaguchi, Kazuya [1 ,2 ]
Mizuno, Noritaka [1 ,2 ]
机构
[1] Univ Tokyo, Sch Engn, Dept Appl Chem, Bunkyo Ku, Tokyo 1138656, Japan
[2] Japan Sci & Technol Agcy, CREST, Kawaguchi, Saitama 3320012, Japan
关键词
aldehydes; aldoximes; heterogeneous catalysis; primary amides; rhodium hydroxide;
D O I
10.1002/asia.200800067
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A supported rhodium hydroxide catalyst, Rh(OH)(x)/Al2O3 (X = 3), is prepared by the reaction of Al2O3 with RhCl3 in an aqueous medium followed by treatment with NaOH. The Rh-III hydroxide species is monomerically (or highly) dispersed on the Al2O3 support. Rh(OH)(x)/Al2O3 acts as a reusable heterogeneous catalyst in water, rather than in an explosive, hazardous, and carcinogenic organic solvent, for the synthesis of primary amides from aldoximes or aldehydes by an efficient sequential process of dehydration and rehydration. The dehydrative condensation of aldehydes and hydroxylamine is also promoted by the Rh(OH)(x)/Al2O3 catalyst.
引用
收藏
页码:1715 / 1721
页数:7
相关论文
共 57 条
[1]   The role of catalysis in the design, development, and implementation of green chemistry [J].
Anastas, PT ;
Bartlett, LB ;
Kirchhoff, MM ;
Williamson, TC .
CATALYSIS TODAY, 2000, 55 (1-2) :11-22
[2]  
Anastas PT., 1998, Principles of green chemistry
[3]  
[Anonymous], 2001, FINE CHEM HETEROGENE
[4]  
Beckmann E., 1886, BER DTSCH CHEM GES, V19, P988, DOI DOI 10.1002/CBER.188601901222
[5]  
Briggs D., 1983, Practical Surface Analysis by Auger and X-ray Photoelectron Spectroscopy
[6]   Beckmann reaction of oximes catalysed by chloral: mild and neutral procedures [J].
Chandrasekhar, S ;
Gopalaiah, K .
TETRAHEDRON LETTERS, 2003, 44 (04) :755-756
[7]  
Connors K. A., 1990, CHEM KINETICS STUDY
[8]   Beckmann rearrangement of oximes under very mild conditions [J].
De Luca, L ;
Giacomelli, G ;
Porcheddu, A .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) :6272-6274
[9]  
Fujiwara H., 2007, Angew. Chem, V119, P5294
[10]   A one-pot synthesis of primary amides from aldoximes or aldehydes in water in the presence of a supported rhodium catalyst [J].
Fujiwara, Hiroshi ;
Ogasawara, Yoshiyuki ;
Yamaguchi, Kazuya ;
Mizuno, Noritaka .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (27) :5202-5205