J. B. Fuller, S. M. Williamson, B. Singaram
Sep 1, 1994
Citations
0
Influential Citations
5
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract Pentafluorophenol acts as an efficient proton source for sodium borohydride reductions in diethyl ether containing methanol. This system allows for the regioselective reduction of α,β-unsaturated carbonyl compounds to the corresponding allylic alcohols in high yield. Use of either 1-hexene or N,N,N',N'-tetramethylethylenediamine as borane scavengers moderately improved the regioselectivity of this reaction. Fortunately, sodium trispentafluorophenoxyborohydride, generated in situ, gave regiospecific 1,2-reduction of α,β,-unsaturated carbonyl compounds.