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Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles

Yifeng Chen, Justin P. Romaire and Timothy R. Newhouse*

*Department of Chemistry, Yale University, 275 Prospect Street, New Haven, Connecticut 06520-8107, United States, Email:

Y. Chen, J. P. Romaire, T. R. Newhouse, J. Am. Chem. Soc., 2015, 137, 5875-5878.

DOI: 10.1021/jacs.5b02243

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A highly practical and general palladium-catalyzed α,β-dehydrogenation of esters and nitriles gives synthetically useful yields of α,β-unsaturated esters, lactones, and nitriles via generation of a zinc enolate or (cyanoalkyl)zinc species followed by the addition of an allyl oxidant and a palladium catalyst. Preliminary mechanistic investigations propose reversible β-hydride elimination and turnover-limiting, propene-forming reductive elimination.

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Key Words

α,β-unsaturated esters

ID: J48-Y2015