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

ABSTRACT: We herein disclose the first report of a first-row transition metal-catalyzed ?,?-dehydrogenation of carbonyl compounds using allyl-nickel catalysis. This development overcomes several limitations of previously reported allyl-palladium-catalyzed oxidation, and is further leveraged for the development of an oxidative cycloalkenylation reaction that provides access to bicycloalkenones with fused, bridged, and spirocyclic ring systems using unactivated ketone and alkene precursors.

SUBMITTER: Huang D

PROVIDER: S-EPMC7495923 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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

Huang David D Szewczyk Suzanne M SM Zhang Pengpeng P Newhouse Timothy R TR

Journal of the American Chemical Society 20190325 14

We herein disclose the first report of a first-row transition metal-catalyzed α,β-dehydrogenation of carbonyl compounds using allyl-nickel catalysis. This development overcomes several limitations of previously reported allyl-palladium-catalyzed oxidation, and is further leveraged for the development of an oxidative cycloalkenylation reaction that provides access to bicycloalkenones with fused, bridged, and spirocyclic ring systems using unactivated ketone and alkene precursors. ...[more]

PMID: 30861346

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