Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds

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dc.citation.journalTitleNature Chemistryen_US
dc.contributor.authorGao, Hongyinen_US
dc.contributor.authorZhou, Zheen_US
dc.contributor.authorKwon, Doo-Hyunen_US
dc.contributor.authorCoombs, Jamesen_US
dc.contributor.authorJones, Stevenen_US
dc.contributor.authorBehnke, Nicole Erinen_US
dc.contributor.authorEss, Daniel H.en_US
dc.contributor.authorKürti, Lászlóen_US
dc.contributor.orgBioScience Research Collaborativeen_US
dc.date.accessioned2017-01-27T19:05:16Z
dc.date.available2017-01-27T19:05:16Z
dc.date.issued2016en_US
dc.description.abstractArylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C−C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (−NH2) and hydroxyl (−OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N−H and N−alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.en_US
dc.identifier.citationGao, Hongyin, Zhou, Zhe, Kwon, Doo-Hyun, et al.. "Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds." <i>Nature Chemistry,</i> (2016) Springer Nature: http://dx.doi.org/10.1038/nchem.2672.
dc.identifier.doihttp://dx.doi.org/10.1038/nchem.2672en_US
dc.identifier.urihttps://hdl.handle.net/1911/93784
dc.language.isoengen_US
dc.publisherSpringer Nature
dc.rightsThis is an author's peer-reviewed final manuscript, as accepted by the publisher. The published article is copyrighted by Springer Nature.en_US
dc.titleRapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffoldsen_US
dc.typeJournal articleen_US
dc.type.dcmiTexten_US
dc.type.publicationpost-printen_US
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