Selective Aldehyde Reduction in Ketoaldehydes with NaBH₄-Na₂CO₃-H₂O at Room Temperatures

Abstract

A variety of aliphatic and aromatic ketoaldehydes were reduced to the corresponding ketoalcohols with a mixture of sodium borohydride (1.2 equivalents) and sodium carbonate (sixfold molar excess) in water. Reactions were performed at room temperatures over (typically) 2 h, and yields of isolated products generally ranged from 70% to 85%. A bis-carbonate-borane complex, [(BH₃)₂CO₂]²⁻ 2Na⁺, possibly formed from the reagent mixture, is likely the active reductant. The moderated reactivity of this acylborane species would explain the chemoselectivity observed in the reactions. The readily available reagents and the mild aqueous conditions make for ease of operation and environmental compatibility, and make a useful addition to available methodology.

GRAPHICAL ABSTRACT

Keywords:

• Acylborane
• aldehyde
• aqueous
• borane
• borohydride
• chemoselective
• reduction