title: Benzylation Reactions in DMF Lead to an Impurity Which Acts as an Organocatalyst Poison in Thiourea-Catalyzed Glycosylations.
abstract: The benzylation of alcohols with the commonly used combination of benzyl bromide and sodium hydride in DMF can lead to the formation of an amine side product, N,N'-dimethyl-1-phenyl-1-(o-tolyl)methanamine. This amine coeluted with benzylated galactal during column chromatography and was found to be a catalyst poison in thiourea-catalyzed glycosylations of galactals. It may also be problematic for other base-sensitive reactions involving benzylated substrates. Solutions to this problem are described.
authors: Centre for Synthesis and Chemical Biology, UCD School of Chemistry, University College Dublin , Belfield, Dublin 4, Ireland.
authors: Avene C
authors: AC
authors: Colgan
authors: Centre for Synthesis and Chemical Biology, UCD School of Chemistry, University College Dublin , Belfield, Dublin 4, Ireland.
authors: Helge
authors: H
authors: Müller-Bunz
authors: Centre for Synthesis and Chemical Biology, UCD School of Chemistry, University College Dublin , Belfield, Dublin 4, Ireland.
authors: Eoghan M
authors: EM
authors: McGarrigle