Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides

Jeffrey S Quesnel; Laure V Kayser; Alexander Fabrikant; Bruce A Arndtsen

doi:10.1002/chem.201500476

Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides

Chemistry. 2015 Jun 22;21(26):9550-5. doi: 10.1002/chem.201500476. Epub 2015 May 15.

Authors

Jeffrey S Quesnel¹, Laure V Kayser¹, Alexander Fabrikant¹, Bruce A Arndtsen²

Affiliations

¹ Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, H3A 0B8 Quebec (Canada).
² Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, H3A 0B8 Quebec (Canada). bruce.arndtsen@mcgill.ca.

PMID: 25982536
DOI: 10.1002/chem.201500476

Abstract

We report a palladium-catalyzed method to synthesize acid chlorides by the chlorocarbonylation of aryl bromides. Mechanistic studies suggest the combination of sterically encumbered PtBu3 and CO coordination to palladium can rapidly equilibrate the oxidative addition/reductive elimination of carbon-halogen bonds. This provides a useful method to assemble highly reactive acid chlorides from stable and available reagents, and can be coupled with subsequent nucleophilic reactions to generate new classes of carbonylated products.

Keywords: acid chloride; carbonylation; mechanism; palladium; reductive elimination.