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Establishment of Broadly Applicable Reaction Conditions for the Palladium-Catalyzed Direct Arylation of Heteroatom-Containing Aromatic Compounds

Benoît Liégault*, David Lapointe, Laurence Caron, Anna Vlassova and Keith Fagnou

*Center for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, ON K1N 6N5, Canada, Email: bliegauluottawa.ca

B. Liégault, D. Lapointe, L. Caron, A. Vlassova, K. Fagnou, J. Org. Chem., 2009, 74, 1826-1834.

DOI: 10.1021/jo8026565 (free Supporting Information)


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Abstract

Conditions for the palladium-catalyzed direct arylation of a wide range of heterocycles with aryl bromides employ a stoichiometric ratio of both coupling partners, as well as a substoichiometric quantity of pivalic acid, which results in significantly faster reactions. An evaluation of the influence of the nature of the aryl halide has also been carried out.

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Key Words

Thiophenes, Benzothiophenes, Thiazoles, Indolizines, Triazoles


ID: J42-Y2009-0660