A novel palladium-catalyzed arylation of ketone enolates with o-nitrohaloarenes was achieved through the addition of phenol additives. The mild reaction conditions employed allowed for the inclusion of a wide variety of functional groups in both substrates to be tolerated. The products of this reaction were then readily reductively cyclized to give highly substituted indoles in moderate to excellent overall yields.
“An Annulative Approach to Highly Substituted Indoles: Unusual Effect of Phenolic Additives on the Success of the Arylation of Ketone Enolates”, J. Am. Chem. Soc., 2002, 124(51), 15168-15169.