Issue 1, 2016

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
10 Aug 2015
Accepted
30 Sep 2015
First published
30 Sep 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2016,7, 295-300

Author version available

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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