Organoselenium-catalyzed mild dehydration of aldoximes: an unexpected practical method for organonitrile synthesis

Lei Yu; Hongyan Li; Xu Zhang; Jianqing Ye; Jianping Liu; Qing Xu; Mark Lautens

doi:10.1021/ol500075h

Organoselenium-catalyzed mild dehydration of aldoximes: an unexpected practical method for organonitrile synthesis

Org Lett. 2014 Mar 7;16(5):1346-9. doi: 10.1021/ol500075h. Epub 2014 Feb 24.

Authors

Lei Yu¹, Hongyan Li, Xu Zhang, Jianqing Ye, Jianping Liu, Qing Xu, Mark Lautens

Affiliation

¹ Zhejiang Key Laboratory of Carbon Materials, College of Chemistry and Materials Engineering, Wenzhou University , Wenzhou, Zhejiang 325035, China.

PMID: 24564392
DOI: 10.1021/ol500075h

Abstract

Areneselenenic acids (ArSeOH), readily generated from diaryl diselenides and H2O2 by in situ oxidation, were found to be effective and reusable catalysts for dehydration of aldoximes, leading to a practical and scalable preparation of useful organonitriles under mild conditions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Dehydration
Hydrogen Peroxide / chemistry
Molecular Structure
Nitriles / chemical synthesis*
Nitriles / chemistry
Organoselenium Compounds / chemical synthesis*
Organoselenium Compounds / chemistry
Oxidation-Reduction
Oximes / chemistry*

Substances

Nitriles
Organoselenium Compounds
Oximes
Hydrogen Peroxide