Convenient Reduction of Carbonyl Compounds to their Corresponding Alcohols with NaBH4/(NH4)2C2O4 System

  • D Setamdideh
  • S Ghahremani
Keywords: Sodium borohydride, reduction, carbonyl compounds, ammonium oxalate, chemoselective, regioselectivity

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, α-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

Published
2015-10-13
Section
Articles

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eISSN: 0379-4350