Dirhodium-catalyzed C-H arene amination using hydroxylamines

Mahesh P. Paudyal, Adeniyi Michael Adebesin, Scott R. Burt, Daniel H. Ess, Zhiwei Ma, László Kürti, J R Falck

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97 Scopus citations

Abstract

Primary 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 applicablemethods 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.

Original languageEnglish (US)
Pages (from-to)1144-1147
Number of pages4
JournalScience
Volume353
Issue number6304
DOIs
StatePublished - Sep 9 2016

ASJC Scopus subject areas

  • Medicine(all)
  • General

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    Paudyal, M. P., Adebesin, A. M., Burt, S. R., Ess, D. H., Ma, Z., Kürti, L., & Falck, J. R. (2016). Dirhodium-catalyzed C-H arene amination using hydroxylamines. Science, 353(6304), 1144-1147. https://doi.org/10.1126/science.aaf8713