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Palladium-catalyzed oxidative carbonylation of N-aryl enamino esters with CO and alcohols: synthesis of N-aryl aminomethylenemalonates

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Abstract

A novel palladium-catalyzed regioselective oxidative carbonylation of tri-substituted alkenes with CO and alcohols for the synthesis of α,β-unsaturated esters has been developed. Experimental studies and DFT calculations suggested that the reaction proceeded through alkoxylation of the palladium(II) catalyst, CO and C[double bond, length as m-dash]C double bond migratory insertion, β-(N)H elimination and tautomerization cascade steps. The reaction tolerates a wide range of groups and produces valuable aminomethylenemalonates in high yields.

Graphical abstract: Palladium-catalyzed oxidative carbonylation of N-aryl enamino esters with CO and alcohols: synthesis of N-aryl aminomethylenemalonates

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Publication details

The article was received on 13 Apr 2017, accepted on 10 May 2017 and first published on 10 May 2017


Article type: Communication
DOI: 10.1039/C7CC02852K
Citation: Chem. Commun., 2017, Advance Article
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    Palladium-catalyzed oxidative carbonylation of N-aryl enamino esters with CO and alcohols: synthesis of N-aryl aminomethylenemalonates

    M. Chen, L. Yu, Z. Ren, Y. Wang and Z. Guan, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC02852K

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