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Issue 22, 2018
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Copper-mediated reduction of azides under seemingly oxidising conditions: catalytic and computational studies

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Abstract

The reduction of aryl azides in the absence of an obvious reducing agent is reported. Careful catalyst design led to the production of anilines in the presence of water and air. The reaction medium (toluene/water) is crucial for the success of the reaction, as DFT calculations support the formation of benzyl alcohol as the oxidation product. A singular catalytic cycle is presented for this transformation based on four key steps: nitrene formation through nitrogen extrusion, formal oxidative addition of water, C(sp3)–H activation of toluene and reductive elimination.

Graphical abstract: Copper-mediated reduction of azides under seemingly oxidising conditions: catalytic and computational studies

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Publication details

The article was received on 15 Mar 2018, accepted on 29 Aug 2018 and first published on 16 Oct 2018


Article type: Paper
DOI: 10.1039/C8CY00515J
Catal. Sci. Technol., 2018,8, 5763-5773
  • Open access: Creative Commons BY license
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    Copper-mediated reduction of azides under seemingly oxidising conditions: catalytic and computational studies

    B. Zelenay, M. Besora, Z. Monasterio, D. Ventura-Espinosa, A. J. P. White, F. Maseras and S. Díez-González, Catal. Sci. Technol., 2018, 8, 5763
    DOI: 10.1039/C8CY00515J

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