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Formamide Synthesis through Borinic Acid Catalysed Transamidation under Mild Conditions
dc.contributor.authorDine, Tharwat Mohy El
dc.contributor.authorEvans, David
dc.contributor.authorRouden, Jacques
dc.contributor.authorBlanchet, Jérôme
dc.date.accessioned2017-06-16T20:16:42Z
dc.date.available2017-06-16T20:16:42Z
dc.date.issued2016-04-18
dc.identifier.citationDine, Tharwat Mohy El; Evans, David; Rouden, Jacques; Blanchet, Jérôme (2016). "Formamide Synthesis through Borinic Acid Catalysed Transamidation under Mild Conditions." Chemistry – A European Journal 22(17): 5894-5898.
dc.identifier.issn0947-6539
dc.identifier.issn1521-3765
dc.identifier.urihttps://hdl.handle.net/2027.42/137604
dc.description.abstractA highly efficient and mild transamidation of amides with amines co‐catalysed by borinic acid and acetic acid has been reported. A wide range of functionalised formamides was synthesized in excellent yields, including important chiral α‐amino acid derivatives, with minor racemisation being observed. Experiments suggested that the reaction rely on a cooperative catalysis involving an enhanced boron‐derived Lewis acidity rather than an improved Brønsted acidity of acetic acid.Amide bonds are reputedly difficult to activate due to their high resonance stabilization. An unusual mild activation of dimethylformamide and formamide by borinic acid 1 (see scheme), illustrated by a general formylation of a wide range of amines, including chiral α‐amino esters, has been reported.
dc.publisherWiley
dc.subject.othertransamidation
dc.subject.othersynthetic methods
dc.subject.otherboronic acid
dc.subject.otheramines
dc.subject.otheramides
dc.titleFormamide Synthesis through Borinic Acid Catalysed Transamidation under Mild Conditions
dc.typeArticleen_US
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137604/1/chem201600234-sup-0001-misc_information.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137604/2/chem201600234_am.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137604/3/chem201600234.pdf
dc.identifier.doi10.1002/chem.201600234
dc.identifier.sourceChemistry – A European Journal
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dc.owningcollnameInterdisciplinary and Peer-Reviewed


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