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

被引:73
|
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
下载
收藏
页码:1715 / 1721
页数:7
相关论文
共 50 条
  • [1] A one-pot synthesis of primary amides from aldoximes or aldehydes in water in the presence of a supported rhodium catalyst
    Fujiwara, Hiroshi
    Ogasawara, Yoshiyuki
    Yamaguchi, Kazuya
    Mizuno, Noritaka
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (27) : 5202 - 5205
  • [2] An efficient and improved method for the preparation of nitrites from primary amides and aldoximes
    Narsaiah, AV
    Nagaiah, K
    ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (11) : 1271 - 1274
  • [3] Hexagonal Mesoporous Silica-Supported Copper Oxide (CuO/HMS) Catalyst: Synthesis of Primary Amides from Aldehydes in Aqueous Medium
    Kadam, Ravishankar G.
    Rathi, Anuj K.
    Cepe, Klara
    Zboril, Radek
    Varma, Rajender S.
    Gawande, Manoj B.
    Jayaram, Radha V.
    CHEMPLUSCHEM, 2017, 82 (03): : 467 - 473
  • [4] Heterogeneously Catalyzed Efficient Oxygenation of Primary Amines to Amides by a Supported Ruthenium Hydroxide Catalyst
    Kim, Jung Won
    Yamaguchi, Kazuya
    Mizuno, Noritaka
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (48) : 9249 - 9251
  • [5] Synthesis of Nitriles from Aldoximes and Primary Amides Using XtalFluor-E
    Keita, Massaba
    Vandamme, Mathilde
    Paquin, Jean-Francois
    SYNTHESIS-STUTTGART, 2015, 47 (23): : 3758 - 3766
  • [6] FeIII-Catalyzed Synthesis of Primary Amides from Aldehydes
    Gowda, Ravikumar R.
    Chakraborty, Debashis
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (12) : 2226 - 2229
  • [7] Synthesis of Nitriles from Primary Amides or Aldoximes under Conditions of a Catalytic Swern Oxidation
    Ding, Rui
    Liu, Yongguo
    Han, Mengru
    Jiao, Wenyi
    Li, Jiaqi
    Tian, Hongyu
    Sun, Baoguo
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20): : 12939 - 12944
  • [8] Effect of promoters on properties of supported rhodium-based catalyst for synthesis of isononyl-aldehydes
    College of Chemistry and Chemical Engineering, China University of Petroleum, Qingdao 266555, China
    Zhongguo Shiyou Daxue Xuebao (Ziran Kexue Ban), 2009, 2 (134-138):
  • [9] Polyethylene glycol supported phosphorus chloride: An efficient and recyclable catalyst for the preparation of nitriles from aldoximes
    Zhang, Xiao-Lan
    Sheng, Shou-Ri
    Wei, Mei-Hong
    Liu, Xiao-Ling
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2017, 192 (05) : 513 - 517
  • [10] Preparation of One-Carbon Homologated Amides from Aldehydes or Primary Alcohols
    Gupta, Manoj K.
    Li, Zhexi
    Snowden, Timothy S.
    ORGANIC LETTERS, 2014, 16 (06) : 1602 - 1605