Palladium-catalyzed α-arylation of arylketones at low catalyst loadings

Enrico Marelli; Martin Corpet; Sian R Davies; Steven P Nolan

doi:10.1002/chem.201404900

Palladium-catalyzed α-arylation of arylketones at low catalyst loadings

Chemistry. 2014 Dec 22;20(52):17272-6. doi: 10.1002/chem.201404900. Epub 2014 Nov 20.

Authors

Enrico Marelli¹, Martin Corpet, Sian R Davies, Steven P Nolan

Affiliation

¹ EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST (UK).

PMID: 25414140
DOI: 10.1002/chem.201404900

Abstract

A general catalytic protocol for the α-arylation of aryl ketones has been developed. It involves the use of a preformed, bench-stable Pd-N-heterocyclic carbene pre-catalyst bearing IHept as an ancillary ligand, and allows the coupling of various functionalized coupling partners at very low catalyst loading. Careful choice of the solvent/base system was crucial to obtain optimum catalyst performance. The pre-catalyst was also successfully tested in the synthesis of an industrially relevant compound.

Keywords: NHC; catalysts; ketone arylation; monodentate ligands; palladium.