DFT Studies on the Allylation of Styrene Oxide Catalyzed by Indium Nanoparticles (InNPs)

Abstract

Allyl–indium species are known to smoothly react with electrophiles as epoxides. The intrinsic tension of these cyclic systems makes them very reactive starting materials, giving access to more complex products through regioselective ring-opening. In this work, indium nanoparticles (InNPs) were prepared by fast reduction of indium(III) chloride with lithium sand and a catalytic amount of 4,4′-di-tert-butylbiphenyl. InNPs were employed as catalysts for the ring-opening allylation reaction of styrene oxide with allyl or prenylbromide. All the possible reaction paths for the formation of the different alcohols were modeled applying DFT calculations, achieving good correlation between the experimental and computational results.

Keywords

• indium nanoparticles
• epoxides
• allylation
• DFT methods