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

Research output: Contribution to journalArticle

70 Citations (Scopus)

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

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Hydroxylamines
Agrochemicals
Amination
Biological Products
Oxidants
Hydrogen
Temperature
Pharmaceutical Preparations

ASJC Scopus subject areas

  • Medicine(all)
  • General

Cite this

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

Dirhodium-catalyzed C-H arene amination using hydroxylamines. / Paudyal, Mahesh P.; Adebesin, Adeniyi Michael; Burt, Scott R.; Ess, Daniel H.; Ma, Zhiwei; Kürti, László; Falck, J R.

In: Science, Vol. 353, No. 6304, 09.09.2016, p. 1144-1147.

Research output: Contribution to journalArticle

Paudyal, MP, Adebesin, AM, Burt, SR, Ess, DH, Ma, Z, Kürti, L & Falck, JR 2016, 'Dirhodium-catalyzed C-H arene amination using hydroxylamines', Science, vol. 353, no. 6304, pp. 1144-1147. https://doi.org/10.1126/science.aaf8713
Paudyal MP, Adebesin AM, Burt SR, Ess DH, Ma Z, Kürti L et al. Dirhodium-catalyzed C-H arene amination using hydroxylamines. Science. 2016 Sep 9;353(6304):1144-1147. https://doi.org/10.1126/science.aaf8713
Paudyal, Mahesh P. ; Adebesin, Adeniyi Michael ; Burt, Scott R. ; Ess, Daniel H. ; Ma, Zhiwei ; Kürti, László ; Falck, J R. / Dirhodium-catalyzed C-H arene amination using hydroxylamines. In: Science. 2016 ; Vol. 353, No. 6304. pp. 1144-1147.
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