One-pot reduction of alcohols, aldehydes, ketones, and carboxylic acids to alkanes

31 August 2006

Reduction of alcohols, aldehydes, ketones and carboxylic acids with n-butyl silane or diethyl silane in dichloromethane containing a catalytic amount of tri (pentafluorophenyl)borane gives the corresponding alkanes in 70-97% yield. Phenols are converted to silyloxybenzenes, whilst olefins and nitro groups are unaffected.

Reactions require 5-10 mol% of tri(pentafluorophenyl)borane in dichloromethane at room temperature and one equivalent of silane for each alcohol group (2 for each carbonyl group). Reaction times are from 0.5-10 hours depending on the number of alcohol/carbonyl groups present in the substrate.

* C. McRae and R.D. Nimmagadda, Tet. Letts., 2006, 47, 5755-5758.