Efficient and Substrate-Specific Hydration of Nitriles to Amides in Water by Using a CeO2 Catalyst

被引：110

作者：

Tamura, Masazumi ^{[2
]}

Wakasugi, Hiroko ^{[2
]}

Shimizu, Ken-ichi ^{[1
]}

Satsuma, Atsushi ^{[2
]}

机构：

[1] Hokkaido Univ, Catalysis Res Ctr, Sapporo, Hokkaido 0010021, Japan

[2] Nagoya Univ, Dept Mol Design & Engn, Grad Sch Engn, Nagoya, Aichi 4648603, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 41期

关键词：

amides; cerium; hydration; nitriles; synthetic methods; ORTHO-SELECTIVE METHYLATION; CEO2-FE2O3; CATALYSTS; AQUEOUS-MEDIUM; COMPLEXES; PHENOL; SIZE; HYDROXYAPATITE; ORGANONITRILES; HYDROLYSIS; 1-PROPANOL;

D O I：

10.1002/chem.201101576

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

CeO2 acted as a reusable and effective catalyst for the hydration of various nitriles to amides in water under neutral conditions at low temperature (30-100 °C). CeO2 showed notable substrate specificity for nitriles that have a heteroatom adjacent to the α-carbon atom of the CN group (see scheme). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：11428 / 11431

页数：4

共 48 条

[1] Catalytic vapor-phase cyclization of 1,6-hexanediol into cyclopentanone [J].

Akashi, T ;

Sato, S ;

Takahashi, R ;

Sodesawa, T ;

Inui, K .

CATALYSIS COMMUNICATIONS, 2003, 4 (08) :411-416

[2] A facile synthesis of amides by selective hydration of nitriles using modified natural phosphate and hydroxyapatite as new catalysts [J].

Bazi, F ;

El Badaoui, H ;

Tamani, S ;

Sokori, S ;

Solhy, A ;

Macquarrie, DJ ;

Sebti, S .

APPLIED CATALYSIS A-GENERAL, 2006, 301 (02) :211-214

[3] Selective ruthenium-catalyzed hydration of nitriles to amides in pure aqueous medium under neutral conditions [J].

Cadierno, Victorio ;

Francos, Javier ;

Gimeno, Jose .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (22) :6601-6605

[4] Bis(allyl)ruthenium(IV) Complexes Containing Water-Soluble Phosphane Ligands: Synthesis, Structure, and Application as Catalysts in the Selective Hydration of Organonitriles into Amides [J].

Cadierno, Victorio ;

Diez, Josefina ;

Francos, Javier ;

Gimeno, Jose .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (32) :9808-9817

[5] Molecular recognition in homogeneous transition metal catalysis: a biomimetic strategy for high selectivity [J].

Das, Siddartha ;

Brudvig, Gary W. ;

Crabtree, Robert H. .

CHEMICAL COMMUNICATIONS, 2008, (04) :413-424

[6] Dihydrogen-bond-promoted catalysis:: Catalytic hydration of nitriles with the indenylruthenium hydride complex (η5-C9H7)Ru(dppm)H (dppm = bis(diphenylphosphino)methane) [J].

Fung, WK ;

Huang, X ;

Man, ML ;

Ng, SM ;

Hung, MY ;

Lin, ZY ;

Lau, CP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11539-11544

[7] KETONES FROM MONOCARBOXYLIC ACIDS - CATALYTIC KETONIZATION OVER OXIDE SYSTEMS [J].

GLINSKI, M ;

KIJENSKI, J ;

JAKUBOWSKI, A .

APPLIED CATALYSIS A-GENERAL, 1995, 128 (02) :209-217

[8]

Goto A., 2008, ANGEW CHEM, V120, P3663

[9] RhI-catalyzed hydration of organonitriles under ambient conditions [J].

Goto, Akihiro ;

Endo, Kohei ;

Saito, Susumu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (19) :3607-3609

[10] TRANSPORT AND REACTIVITY OF HYDROCARBON MOLECULES IN A SHAPE-SELECTIVE ZEOLITE [J].

HAAG, WO ;

LAGO, RM ;

WEISZ, PB .

FARADAY DISCUSSIONS, 1981, 72 :317-330

← 1 2 3 4 5 →