Practical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon–Nitrogen Bond Formation

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dc.citation.firstpage11184en_US
dc.citation.issueNumber32en_US
dc.citation.journalTitleJournal of the American Chemical Societyen_US
dc.citation.lastpage11196en_US
dc.citation.volumeNumber139en_US
dc.contributor.authorKattamuri, Padmanabha V.en_US
dc.contributor.authorYin, Junen_US
dc.contributor.authorSiriwongsup, Suracheden_US
dc.contributor.authorKwon, Doo-Hyunen_US
dc.contributor.authorEss, Daniel H.en_US
dc.contributor.authorLi, Qunen_US
dc.contributor.authorLi, Guigenen_US
dc.contributor.authorYousufuddin, Muhammeden_US
dc.contributor.authorRichardson, Paul F.en_US
dc.contributor.authorSutton, Scott C.en_US
dc.contributor.authorKürti, Lászlóen_US
dc.date.accessioned2017-11-14T18:08:23Zen_US
dc.date.available2017-11-14T18:08:23Zen_US
dc.date.issued2017en_US
dc.description.abstractGiven the importance of amines in a large number of biologically active natural products, active pharmaceutical ingredients, agrochemicals, and functional materials, the development of efficient C–N bond-forming methods with wide substrate scope continues to be at the frontier of research in synthetic organic chemistry. Here, we present a general and fundamentally new synthetic approach for the direct, transition-metal-free preparation of symmetrical and unsymmetrical diaryl-, arylalkyl-, and dialkylamines that relies on the facile single or double addition of readily available C-nucleophiles to the nitrogen atom of bench-stable electrophilic aminating agents. Practical single and double polarity reversal (i.e., umpolung) of the nitrogen atom is achieved using sterically and electronically tunable ketomalonate-derived imines and oximes. Overall, this novel approach represents an operationally simple, scalable, and environmentally friendly alternative to transition-metal-catalyzed C–N cross-coupling methods that are currently used to access structurally diverse secondary amines.en_US
dc.identifier.citationKattamuri, Padmanabha V., Yin, Jun, Siriwongsup, Surached, et al.. "Practical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon–Nitrogen Bond Formation." <i>Journal of the American Chemical Society,</i> 139, no. 32 (2017) American Chemical Society: 11184-11196. https://doi.org/10.1021/jacs.7b05279.en_US
dc.identifier.digitalFINAL_REVISED_JACS_Nitrogen_Linchpin_and_Umpolung_Manuscript_June_24_2017en_US
dc.identifier.doihttps://doi.org/10.1021/jacs.7b05279en_US
dc.identifier.urihttps://hdl.handle.net/1911/98800en_US
dc.language.isoengen_US
dc.publisherAmerican Chemical Societyen_US
dc.rightsThis is an author's peer-reviewed final manuscript, as accepted by the publisher. The published article is copyrighted by the American Chemical Society.en_US
dc.titlePractical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon–Nitrogen Bond Formationen_US
dc.typeJournal articleen_US
dc.type.dcmiTexten_US
dc.type.publicationpost-printen_US
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