Benzylation Reactions in DMF Lead to an Impurity Which Acts as an Organocatalyst Poison in Thiourea-Catalyzed Glycosylations

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Title: Benzylation Reactions in DMF Lead to an Impurity Which Acts as an Organocatalyst Poison in Thiourea-Catalyzed Glycosylations
Authors: Colgan, Avene C.
Müller-Bunz, Helge
McGarrigle, Eoghan M.
Permanent link: http://hdl.handle.net/10197/9468
Date: 25-Oct-2016
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.
Funding Details: Irish Research Council
Science Foundation Ireland
Type of material: Journal Article
Publisher: ACS
Journal: Journal of Organic Chemistry
Volume: 81
Issue: 22
Start page: 11394
End page: 11396
Copyright (published version): 2016 American Chemical Society
Keywords: Clinical SciencesBenzylationGlycosylationImpuritiesThiourea
DOI: 10.1021/acs.joc.6b01914
Language: en
Status of Item: Peer reviewed
Appears in Collections:Chemistry Research Collection

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