Straightforward zinc-catalyzed transformation of aldehydes and hydroxylamine hydrochloride to nitriles

被引：37

作者：

Enthaler, Stephan ^{[1
]}

Weidauer, Maik ^{[1
]}

Schroeder, Fanny ^{[1
]}

机构：

[1] Tech Univ Berlin, Dept Chem, D-10623 Berlin, Germany

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 07期

关键词：

Catalysis; Zinc; Nitriles; Aldoximes; Dehydration; ASYMMETRIC HYDROSILYLATION; ENANTIOSELECTIVE HYDROSILYLATION; CARBONYL-COMPOUNDS; HIGHLY EFFICIENT; GREEN CHEMISTRY; CHIRAL LIGANDS; KETONES; REDUCTION; POLYMETHYLHYDROSILOXANE; CONVERSION;

D O I：

10.1016/j.tetlet.2011.12.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the present study, the zinc-catalyzed dehydration of a range of in situ generated aldoximes, available by the reaction of aldehydes and hydroxylamine hydrochloride, has been explored. After investigating various reaction parameters, with Zn(OTf)(2) an excellent and easily accessible pre-catalyst was obtained. The system was highly active and dehydrated a broad range of aldoximes selectively to the corresponding nitriles under mild reaction conditions. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：882 / 885

页数：4

共 43 条

[1] 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

[2] Origins, current status, and future challenges of green chemistry [J].

Anastas, PT ;

Kirchhoff, MM .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) :686-694

[3] Catalysis as a foundational pillar of green chemistry [J].

Anastas, PT ;

Kirchhoff, MM ;

Williamson, TC .

APPLIED CATALYSIS A-GENERAL, 2001, 221 (1-2) :3-13

[4] New chiral diamino-bis(tert-thiophene): an effective ligand for Pd- and Zn-catalyzed asymmetric transformations [J].

Bandini, Marco ;

Melucci, Manuela ;

Piccinelli, Fabio ;

Sinisi, Riccardo ;

Tommasi, Simona ;

Umani-Ronchi, Achille .

CHEMICAL COMMUNICATIONS, 2007, (43) :4519-4521

[5]

Beller M., 2004, TRANSITION METALS OR

[6] Direct Zn-diamine promoted reduction of C=O and C=N bonds by polymethylhydrosiloxane in methanol [J].

Bette, V ;

Mortreux, A ;

Lehmann, CW ;

Carpentier, JF .

CHEMICAL COMMUNICATIONS, 2003, (03) :332-333

[7] [Zinc-diamine]-catalyzed hydrosilylation of ketones in methanol. New developments and mechanistic insights [J].

Bette, V ;

Mortreux, A ;

Savoia, D ;

Carpentier, JF .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :289-302

[8] New developments in zinc-catalyzed asymmetric hydrosilylation of ketones with PMHS [J].

Bette, V ;

Mortreux, A ;

Savoia, D ;

Carpentier, JF .

TETRAHEDRON, 2004, 60 (12) :2837-2842

[9] New chiral 1,2-diamines and their use in zinc-catalyzed asymmetric hydrosilylation of acetophenone [J].

Bette, V ;

Mortreux, A ;

Ferioli, F ;

Martelli, G ;

Savoia, D ;

Carpentier, JF .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (14) :3040-3045

[10]

Cornils B, 2005, MULTIPHASE HOMOGENEOUS CATALYSIS, VOLS 1 AND 2, P1, DOI 10.1002/9783527619597

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