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Switchable Selectivity in the Pd-Catalyzed Alkylative Cross-Coupling of Esters

Jeanne Masson-Makdissi, Jaya Kishore Vandavasi and Stephen G. Newman*

*Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada, Email:

J. Masson-Makdissi, J. K. Vandavasi, S. G. Newman, Org. Lett., 2018, 20, 4094-4098.

DOI: 10.1021/acs.orglett.8b01646

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Using a Pd-NHC catalyst for cross-coupling of phenyl esters and alkyl boranes, alkyl ketones can be prepared in good yields via a Suzuki-Miyaura reaction proceeding by activation of the C(acyl)-O bond, whereas a Pd-dcype catalyst provides alkylated arenes by a modified pathway with extrusion of CO.

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Key Words

Suzuki coupling, ketones

ID: J54-Y2018