Conversion of aldoximes into nitriles and amides under mild conditions

被引：46

作者：

Tambara, Koujiro ^{[1
]}

Pantos, G. Dan ^{[2
]}

机构：

[1] Univ Cambridge, Univ Chem Lab, Cambridge CB2 1EW, England

[2] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 15期

基金：

英国工程与自然科学研究理事会;

关键词：

CATALYZED ONE-POT; ALDEHYDES; RUBBER; REARRANGEMENT; OXIMES; METAL;

D O I：

10.1039/c3ob27362h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of Pd(en)X-2 salts were used as catalysts for the conversion of aldoximes into nitriles and amides. Highlights of this protocol include the use of inexpensive polar solvents, including water, and moderate reaction temperatures. A high degree of selectivity in the reaction outcome was observed when using aliphatic vs. aromatic/conjugated aldoximes.

引用

页码：2466 / 2472

页数：7

共 30 条

[1]

Achary PS, 2001, J APPL POLYM SCI, V81, P2597

[2] Palladium-Catalyzed One-Pot Conversion of Aldehydes to Amides [J].

Ali, Md Ashif ;

Punniyamurthy, Tharmalingam .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) :288-292

[3] Mechanistic Studies into Metal-Catalyzed Aldoxime to Amide Rearrangements [J].

Allen, C. Liana ;

Lawrence, Ruth ;

Emmett, Liam ;

Williams, Jonathan M. J. .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (18) :3262-3268

[4] Metal-catalysed approaches to amide bond formation [J].

Allen, C. Liana ;

Williams, Jonathan M. J. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3405-3415

[5] Catalytic Acylation of Amines with Aldehydes or Aldoximes [J].

Allen, C. Liana ;

Davulcu, Simge ;

Williams, Jonathan M. J. .

ORGANIC LETTERS, 2010, 12 (22) :5096-5099

[6] Cost efficient synthesis of amides from oximes with indium or zinc catalysts [J].

Allen, C. Liana ;

Burel, Celine ;

Williams, Jonathan M. J. .

TETRAHEDRON LETTERS, 2010, 51 (20) :2724-2726

[7] Analysis of the reactions used for the preparation of drug candidate molecules [J].

Carey, John S. ;

Laffan, David ;

Thomson, Colin ;

Williams, Mike T. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347

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

Fujiwara, Hiroshi ;

Ogasawara, Yoshiyuki ;

Kotani, Miyuki ;

Yamaguchi, Kazuya ;

Mizuno, Noritaka .

CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (8-9) :1715-1721

[9] 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

[10] Ruthenium-Catalyzed Rearrangement of Aldoximes to Primary Amides in Water [J].

Garcia-Alvarez, Rocio ;

Diaz-Alvarez, Alba E. ;

Borge, Javier ;

Crochet, Pascale ;

Cadierno, Victorio .

ORGANOMETALLICS, 2012, 31 (17) :6482-6490

← 1 2 3 →