Taylor & Francis Group
Browse
lsyc_a_888751_sm0216.pdf (193.41 kB)

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

Download (0 kB)
Version 2 2014-06-09, 18:53
Version 1 2014-06-09, 18:53
journal contribution
posted on 2014-06-09, 18:53 authored by Sosale Chandrasekhar, Annadka Shrinidhi

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.

History

Usage metrics

    Synthetic Communications

    Categories

    Licence

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC