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TEMPO-Me: An Electrochemically Activated Methylating Agent

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dc.contributor.authorNorcott, Philip
dc.contributor.authorHammill, Chelsey
dc.contributor.authorNoble, Dr Benjamin
dc.contributor.authorRobertson, Johnathon C
dc.contributor.authorOlding, Angus
dc.contributor.authorBissember, Alex C
dc.contributor.authorCoote, Michelle
dc.date.accessioned2020-08-28T05:05:38Z
dc.date.issued2019-09-04
dc.description.abstractBench- and air-stable 1-methoxy-2,2,6,6-tetramethylpiperidine (TEMPO-Me) is relatively unreactive at ambient temperature in the absence of an electrochemical stimulus. In this report, we demonstrate that the one-electron electrochemical oxidation of TEMPO-Me produces a powerful electrophilic methylating agent in situ. Our computational and experimental studies are consistent with methylation proceeding via a SN2 mechanism, with a strength comparable to the trimethyloxonium cation. A protocol is developed for the electrochemical methylation of aromatic acids using TEMPO-Me.en_AU
dc.description.sponsorshipAustralian Research Council (FL170100041, CE140100012)en_AU
dc.format.mimetypeapplication/pdfen_AU
dc.identifier.issn0002-7863en_AU
dc.identifier.urihttp://hdl.handle.net/1885/209107
dc.language.isoen_AUen_AU
dc.provenancehttps://v2.sherpa.ac.uk/id/publication/7788..."The Accepted Version can be archived in a non-commercial institutional repository. 12 months embargo." from SHERPA/RoMEO site (as at 28/08/2020)." This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of organic chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://dx.doi.org/10.1021/jacs.9b08634en_AU
dc.publisherAmerican Chemical Societyen_AU
dc.relationhttp://purl.org/au-research/grants/arc/FL170100041en_AU
dc.relationhttp://purl.org/au-research/grants/arc/CE140100012en_AU
dc.rights© 2019 American Chemical Societyen_AU
dc.sourceJournal of the American Chemical Societyen_AU
dc.titleTEMPO-Me: An Electrochemically Activated Methylating Agenten_AU
dc.typeJournal articleen_AU
dcterms.accessRightsOpen Accessen_AU
local.bibliographicCitation.issue38en_AU
local.bibliographicCitation.lastpage15455en_AU
local.bibliographicCitation.startpage15450en_AU
local.contributor.affiliationNorcott, P., Research School of Chemistry, The Australian National Universityen_AU
local.contributor.affiliationHammill, C., Research School of Chemistry, The Australian National Universityen_AU
local.contributor.affiliationNoble, B., Research School of Chemistry, The Australian National Universityen_AU
local.contributor.affiliationCoote, Michelle, Research School of Chemistry, The Australian National Universityen_AU
local.contributor.authoruidU4524714en_AU
local.identifier.citationvolume141en_AU
local.identifier.doi10.1021/jacs.9b08634en_AU
local.identifier.essn1520-5126en_AU
local.publisher.urlhttp://pubs.acs.org/journal/jacsat/about.htmlen_AU
local.type.statusAccepted Versionen_AU

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