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dc.contributor.authorGao, Hongyin
Zhou, Zhe
Kwon, Doo-Hyun
Coombs, James
Jones, Steven
Behnke, Nicole Erin
Ess, Daniel H.
Kürti, László
dc.date.accessioned 2017-01-27T19:05:16Z
dc.date.available 2017-01-27T19:05:16Z
dc.date.issued 2016
dc.identifier.citation Gao, Hongyin, Zhou, Zhe, Kwon, Doo-Hyun, et al.. "Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds." Nature Chemistry, (2016) Springer Nature: http://dx.doi.org/10.1038/nchem.2672.
dc.identifier.urihttps://hdl.handle.net/1911/93784
dc.description.abstract Arylmetals 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.
dc.language.iso eng
dc.publisher Springer Nature
dc.rights This is an author's peer-reviewed final manuscript, as accepted by the publisher. The published article is copyrighted by Springer Nature.
dc.title Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds
dc.type Journal article
dc.citation.journalTitle Nature Chemistry
dc.contributor.org BioScience Research Collaborative
dc.type.dcmi Text
dc.identifier.doihttp://dx.doi.org/10.1038/nchem.2672
dc.type.publication post-print


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