4.8 Article

Palladium-Catalyzed Cyclocarbonylation-Decarboxylation of Diethyl(2-iodoaryl)malonates with Vinyl Ketones Affording Functionalized Enolic 2-Acyl-3,4-dihydronaphthalenones

Journal

ORGANIC LETTERS
Volume 11, Issue 15, Pages 3278-3281

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol900859n

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Funding

  1. Natural Sciences and Engineering Research Council of Canada (NSERC)

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A wide variety of enolic tautomers of functionalized 2-acyl-3,4-dihydronaphthalen-1(2H)-ones were obtained in moderate to excellent yields by the palladium-catalyzed cyclocarbonylation-decarboxylation of diethyl(2-iodoaryl)malonates with vinyl ketones and carbon monoxide. The reaction may proceed via the formation of a keto-diester, followed by oxidative addition, CO insertion, intramolecular cyclization, and decarboxylation to give the enolic substituted 2-acyldihydronaphthalenones.

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