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Allyl-Nickel Catalysis Enables Carbonyl Dehydrogenation and Oxidative Cycloalkenylation of Ketones

David Huang, Suzanne M. Szewczyk, Pengpeng Zhang, Timothy R. Newhouse*

*Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States, Email: timothy.newhouseyale.edu

D. Huang, S. M. Szewczyk, P. Zhang, T. R. Newhouse, J. Am. Chem. Soc., 2019, 141, 5669-5674.

DOI: 10.1021/jacs.9b02552 (free Supporting Information)



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Abstract

Allyl-nickel catalysis enables α,β-dehydrogenation of carbonyl compounds. In addition, an oxidative cycloalkenylation reaction provides access to bicycloalkenones with fused, bridged, and spirocyclic ring systems using unactivated ketone and alkene precursors.

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Key Words

enones, alkenyl nitriles, unsaturated esters, diethyl allyl phosphate


ID: J48-Y2019