Solvent-Dependent Substrate Reduction by {Sm[N(SiMe3)2]2(THF)2}. An Alternative Approach for Accelerating the Rate of Substrate Reduction by Sm(II)

TitleSolvent-Dependent Substrate Reduction by {Sm[N(SiMe3)2]2(THF)2}. An Alternative Approach for Accelerating the Rate of Substrate Reduction by Sm(II)
Publication TypeJournal Article
Year of Publication2014
AuthorsChciuk TV, Hilmersson G, Flowers, II RA
JournalJournal of Organic Chemistry
Volume79
Issue20
Start Page9441
Pagination9443
Date Published09/2014
Type of ArticleBrief Communication
Abstract

The impact of solvent on electron transfer from Sm(II) to substrates was measured by determining the rate of reduction of 1-bromo-, 1-chlorododecane, and 3-pentanone in THF and hexanes using the highly soluble reductant {Sm[N(SiMe3)2]2(THF)2}. Rates were found to be 3 orders of magnitude faster in hexanes than THF, and reductions of alkyl halides were inverse first order in THF. These findings show the solvent milieu significantly impacts the rate of substrate reduction, a consideration that may prove useful in synthesis.