figshare
Browse
lsyc_a_909489_sm4708.pdf (388 kB)

Hydrogenation of Aldehydes and Ketones to Corresponding Alcohols with Methylamine Borane in Neat Water

Download (0 kB)
Version 3 2014-07-09, 01:13
Version 2 2014-07-09, 01:13
Version 1 2014-07-09, 01:13
journal contribution
posted on 2014-07-09, 01:13 authored by Yifan Duan, Ruijiao Bai, Jun Tian, Ligong Chen, Xilong Yan

Chemoselective hydrogenation of various aldehydes and ketones with methylamine borane (MeAB) in neat water was investigated. MeAB is suitable for green organic reactions, for MeAB is a nontoxic, environmentally benign, and easily handled reagent. Aldehydes were selectively and rapidly hydrogenated in excellent yields (86–97%) for 30 min, but hydrogenation of aromatic ketones needed over 20 h at room temperature because of their poor water solubility and steric hindrance. Thus we investigated polyethylene glycol (PEG400) and acidic cation-exchange D072 resin as catalysts to accelerate the hydrogenation reaction of aromatic ketones and achieved excellent yields within several hours. PEG 400 and D072 resin are both suitable for green organic reactions. The D072 resin was reused up to four times without any significance loss in activity.

History

Usage metrics

    Synthetic Communications

    Categories

    Licence

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC