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

Abstract

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.

GRAPHICAL ABSTRACT

Keywords:

• Aldehydes
• hydrogenation
• ketones
• methylamine borane
• water

Notes

^a All reactions were carried out with MeAB (1 mmol), aldehyde, or ketone (1 mmol) in H₂O (2 mL) at room temperature.

^b Detected by GC.

^a All reactions were carried out with AB (1 mmol), aldehyde or ketone (1 mmol), and PEG 400 (0.5 mL) in H₂O (2 mL) for 8 h at room temperature.

^b Detected by GC.

^a All reactions were carried out with MeAB (1 mmol), aldehyde or ketone (1 mmol), and D072 resin (0.8 g) in H₂O (2 mL) for 6 h at room temperature.

^b Detected by GC.

^a All reactions were carried out with MeAB (1 mmol), hypnone (1 mmol), and D072 resin (0.8 g) in H₂O (2 mL) at room temperature for 6 h.

^b Detected by GC.

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