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Updated: Jun 11, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Cross-Coupling of Nitroalkanes with Enamides, Enecarbamates, and Enol Ethers
Katarína R Detková1, Alexandra M Liptajová1, Branislav Ferko1
1Department of Organic Chemistry, Slovak University of Technology in Bratislava, Radlinského 9, Bratislava 812 37, Slovakia.
Abstract:
A stepwise cross-coupling of cyclic enamides, enecarbamates, and enol ethers, with functionalized nitroalkanes has been developed, offering access to functionalized tetrahydropyridines, dihydropyrans, and other heterocycles. The outcome of the palladium-free process resembles a Heck-type reaction, in which β-substituted nitroalkanes serve as an acrylate surrogate. The method utilizing the powerful CAN oxidant tolerates several commonly employed protective groups and operates via a well-understood reaction mechanism.
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