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.
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 Sciences; Benzylation; Glycosylation; Impurities; Thiourea||DOI:||10.1021/acs.joc.6b01914||Language:||en||Status of Item:||Peer reviewed|
|Appears in Collections:||Chemistry Research Collection|
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