A general method for the rapid reduction of alkenes and alkynes using sodium borohydride, acetic acid, and palladium

Alkenes and alkynes are rapidly reduced to the corresponding alkanes using sodium borohydride and acetic acid in the presence of a small amount of palladium catalyst. The heterogeneous reaction is conducted in open air at room temperature. Reactions typically afford conversions to the alkane product of 98% or more within 15 min. The best solvent system was determined to be isopropyl alcohol, though reduction also takes place in solvents such as tetrahydrofuran, chloroform and, with some substrates, even in water. The method described is a convenient alternative to hydrogenations that require an external supply of hydrogen gas. (C) 2009 Elsevier Ltd. All rights reserved.