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Issue 1, 2016
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A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts

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Abstract

4-Dimethylaminopyridine (DMAP) is shown to undergo Pd/PtBu3 catalyzed coupling with aryl halides and carbon monoxide to form electrophilic aroyl–DMAP salts. The reaction is easily scalable to prepare multigram quantities with low catalyst loadings, while the precipitation of these salts as they form leads to products with low impurities. These reagents rapidly react with a variety of nucleophiles, including those that contain potentially incompatible functional groups under standard carbonylative conditions.

Graphical abstract: A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts

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Publication details

The article was received on 10 Aug 2015, accepted on 30 Sep 2015 and first published on 30 Sep 2015


Article type: Edge Article
DOI: 10.1039/C5SC02949J
Citation: Chem. Sci., 2016,7, 295-300
  • Open access: Creative Commons BY-NC license
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    A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts

    J. S. Quesnel, A. Fabrikant and B. A. Arndtsen, Chem. Sci., 2016, 7, 295
    DOI: 10.1039/C5SC02949J

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