RESEARCH ARTICLE

 

Convenient reduction of carbonyl compounds to their corresponding alcohols with NaBH₄/(NH₄)₂C₂O₄ system

 

 

Davood Setamdideh^*; Sahar Ghahremani

Department of Chemistry, Faculty of Sciences, Mahabad Branch, Islamic Azad University, 59135-443, Iran

 

 

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ABSTRACT

Sodium borohydride (0.4-1.5 equivalents) in the presence of ammonium oxalate (0.2 equivalents) reduces varieties of organic carbonyl compounds such as aldehydes, ketones, acyloins, a-diketones and α,β-unsaturated carbonyl compounds to their corresponding alcohols. Reduction reactions were carried out in acetonitrile in high to excellent yields of products. The chemoselective reduction of aldehydes over ketones was accomplished successfully with this reducing system. In addition, regioselectivity and exclusive 1,2-reduction of conjugated carbonyl compounds to their corresponding allylic alcohols in high to excellent yields was achieved successfully with this reducing system.

Keywords: Sodium borohydride, reduction, carbonyl compounds, ammonium oxalate, chemoselective, regioselectivity

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Acknowledgements

The authors gratefully acknowledge financial assistance by the research council of the Islamic Azad University branch of Mahabad.

 

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Received 6 January 2012
Revised 14 February 2012
Accepted 17 March 2012

 

 

* To whom correspondence should be addressed. E-mail: davood.setamdideh@gmail.com