Colloidal Palladium Nanoparticles with In Situ H₂: Reducing System for α,β-Unsaturated Carbonyl Compounds

Abstract

A new reducing system comprising Pd(OAc)₂ and NaBH₄ in methanol to generate palladium nanoparticles has been efficiently utilized to reduce a variety of unsaturated carbonyl compounds. These were reduced to their corresponding saturated alcohols and fully saturated compounds in selected cases. This protocol presents alternative and mild reaction conditions for reduction.

Keywords:

• Hydride
• hydrogenation
• palladium nano-sized particle
• saturated alcohol
• α,β-unsaturated carbonyl compounds

ACKNOWLEDGMENTS

K. D. C. acknowledges financial support from the Korean Ministry of Education through the second stage of the BK21 project for the Hanyang University graduate program. This work was supported by the research fund of Hanynag University (HY-2004-I).

Notes

^a Isolated yield.

^b Reacted with 2 equiv. NaBH₄ and 0.05 equiv. Pd(OAc)₂.

^c The substrate was dissolved first in 1 mL methanol before adding 1 equiv. NaBH₄ and 0.05 equiv. Pd(OAc)₂.

^d The substrate was dissolved first in 1 mL chloroform before adding 1 equiv. NaBH₄ and 0.10 equiv. Pd(OAc)₂.

^e The substrate was dissolved first in 1 mL methanol before adding 2 equiv. NaBH₄ and 0.05 equiv. Pd(OAc)₂.