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

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Palladium-catalyzed oxidative carbonylation of N-aryl enamino esters with CO and alcohols: synthesis of N-aryl aminomethylenemalonates
Chemical Communications ( IF 4.3 ) Pub Date : 2017-05-10 00:00:00 , DOI: 10.1039/c7cc02852k
Ming Chen _{1,

2,

3,

4,

5} , Le Yu _{1,

2,

3,

4,

5} , Zhi-Hui Ren _{1,

2,

3,

4,

5} , Yao-Yu Wang _{1,

2,

3,

4,

5} , Zheng-Hui Guan _{1,

2,

3,

4,

5}

Affiliation

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.

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