Palladium-Catalyzed Mono-α-arylation of Acetone with Aryl Halides and Tosylates

Kevin D. Hesp, Rylan J. Lundgren and Mark Stradiotto*

*Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada B3H 4J3, Email: mark.stradiottodal.ca

K. D. Hesp, R. J. Lundgren, M. Stradiotto, J. Am. Chem. Soc., 2011, 133, 5194-5197.

DOI: 10.1021/ja200009c

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Abstract

The use of appropriately designed P,N-ligands proved to be the key to controlling the reactivity and selectivity in Pd-catalyzed mono-α-arylation of acetone with aryl chlorides, bromides, iodides, and tosylates. The reaction affords good yields with substrates containing a range of functional groups at modest Pd loadings using Cs₂CO₃ as the base and employing acetone as both a reagent and the solvent.

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Key Words

α-arylation

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ID: J48-Y2011-0970