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Catalytic Allylic C−H Acetoxylation and Benzoyloxylation via Suggested (η3-Allyl)palladium(IV) Intermediates

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journal contribution
posted on 03.12.2009, 00:00 by Lukasz T. Pilarski, Nicklas Selander, Dietrich Böse, Kálmán J. Szabó
Palladium-catalyzed allylic acetoxylations and benzoyloxylations were carried out using iodonium salts. The reactions proceed under mild conditions with high regio- and stereoselectivity. The catalysis can be performed under both acidic and nonacidic conditions without use of BQ or other external oxidants and activator ligands. Deuterium labeling experiments clearly show that the catalytic reaction proceeds through (η3-allyl)palladium intermediates. A stoichiometric study with one of the catalysts provided evidence for the formation of a Pd(IV) species.