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Effective Palladium-Catalyzed Hydroxycarbonylation of Aryl Halides with Substoichiometric Carbon Monoxide

Signe Korsager, Rolf H. Taaning and Troels Skrydstrup*

*Department of Chemistry and the Interdisciplinary Nanoscience Center, Aarhus University, Gustavs Wieds Vej 14, 8000 Aarhus, Denmark, Email: tschem.au.dk

S. Korsager, R. H. Taaning, T. Skrydstrup, J. Am. Chem. Soc., 2013, 135, 2891-2894.

DOI: 10.1021/ja3114032 (free Supporting Information)


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Abstract

Only 1-5 mol % of CO are needed to enable a Pd-catalyzed hydroxycarbonylation of aryl iodides, bromides, and chlorides in the presence of potassium formate as the only stoichiometric, mildly basic nucleophile and a reservoir of CO. The substoichiometric CO is generated in situ from an acyl-Pd(II) precatalyst, which provides both the CO and an active catalyst, and thereby obviates the need for handling the toxic gas.

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Key Words

Hydroxycarbonylation


ID: J48-Y2013-0450