Issue 35, 2017

Nitrile-assisted oxidation over oxidative-annulation: Pd-catalyzed α,β-dehydrogenation of α-cinnamyl β-keto nitriles

Abstract

A palladium-catalyzed oxidation reaction is disclosed where the nitrile functionality on the substrate simply changes the course of the reaction. Our previous finding showed that using the Pd(II)-catalyst in the presence of benzoquinone as an oxidant, 2-cinnamyl-1,3-dicarbonyls provides functionalized furans via oxidative cyclization. When a nitrile group is replaced with one of the carbonyl functionalities of the same substrate, the oxidative cyclization was completely suppressed; instead, the oxidation at the α,β-position occurred to provide α,β,γ,δ-diene containing β-keto nitriles.

Graphical abstract: Nitrile-assisted oxidation over oxidative-annulation: Pd-catalyzed α,β-dehydrogenation of α-cinnamyl β-keto nitriles

Supplementary files

Article information

Article type
Paper
Submitted
12 เม.ย. 2560
Accepted
09 ส.ค. 2560
First published
09 ส.ค. 2560

Org. Biomol. Chem., 2017,15, 7317-7320

Nitrile-assisted oxidation over oxidative-annulation: Pd-catalyzed α,β-dehydrogenation of α-cinnamyl β-keto nitriles

R. Nallagonda, R. R. Reddy and P. Ghorai, Org. Biomol. Chem., 2017, 15, 7317 DOI: 10.1039/C7OB00912G

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