Dirhodium-catalyzed C-H arene amination using hydroxylamines

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dc.citation.firstpage1144
dc.citation.issueNumber6304
dc.citation.journalTitleScience
dc.citation.lastpage1147
dc.citation.volumeNumber353
dc.contributor.authorPaudyal, Mahesh P.
dc.contributor.authorAdebesin, Adeniyi Michael
dc.contributor.authorBurt, Scott R.
dc.contributor.authorEss, Daniel H.
dc.contributor.authorMa, Zhiwei
dc.contributor.authorKürti, László
dc.contributor.authorFalck, John R.
dc.date.accessioned2017-11-06T21:15:05Z
dc.date.available2017-11-06T21:15:05Z
dc.date.issued2016
dc.description.abstractPrimary and N-alkyl arylamine motifs are key functional groups in pharmaceuticals, agrochemicals, and functional materials, as well as in bioactive natural products. However, there is a dearth of generally applicable methods for the direct replacement of aryl hydrogens with NH2/NH(alkyl) moieties. Here, we present a mild dirhodium-catalyzed C-H amination for conversion of structurally diverse monocyclic and fused aromatics to the corresponding primary and N-alkyl arylamines using NH2/NH(alkyl)-O-(sulfonyl)hydroxylamines as aminating agents; the relatively weak RSO2O-N bond functions as an internal oxidant. The methodology is operationally simple, scalable, and fast at or below ambient temperature, furnishing arylamines in moderate-to-good yields and with good regioselectivity. It can be readily extended to the synthesis of fused N-heterocycles.
dc.identifier.citationPaudyal, Mahesh P., Adebesin, Adeniyi Michael, Burt, Scott R., et al.. "Dirhodium-catalyzed C-H arene amination using hydroxylamines." <i>Science,</i> 353, no. 6304 (2016) AAAS: 1144-1147. https://doi.org/10.1126/science.aaf8713.
dc.identifier.digitalDirhodium_Catalyzed_C-H_Arene_Amination
dc.identifier.doihttps://doi.org/10.1126/science.aaf8713
dc.identifier.urihttps://hdl.handle.net/1911/97831
dc.language.isoeng
dc.publisherAAAS
dc.rightsThis is an author's peer-reviewed final manuscript, as accepted by the publisher. The published article is copyrighted by AAAS.
dc.titleDirhodium-catalyzed C-H arene amination using hydroxylamines
dc.typeJournal article
dc.type.dcmiText
dc.type.publicationpost-print
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