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Ketone Synthesis by a Nickel-Catalyzed Dehydrogenative Cross-Coupling of Primary Alcohols

Thomas Verheyen, Lars van Turnhout, Jaya Kishore Vandavasi, Eric S. Isbrandt, Wim M. De Borggraeve, Stephen G. Newman*

*Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, Ontario Canada, K1N 6N5, Email: stephen.newmanuottawa.ca

T. Verheyen, L. van Turnhout, J. K. Vandavasi, E. S. Isbrandt, W. M. De Borggraeve, S. G. Newman, J. Am. Chem. Soc., 2019, 141, 6869-6874.

DOI: 10.1021/jacs.9b03280 (free Supporting Information)


Abstract

A Ni-catalyzed intermolecular coupling of primary alcohols and organotriflates provides ketones in the presence of acetone. Two competitive oxidation processes, that generate aldehyde in situ via hydrogen transfer oxidation or (pseudo)dehalogenation pathways, are followed by a Ni-catalyzed carbonyl-Heck process.

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Key Words

aryl ketones, acetone


ID: J48-Y2019