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

Author:
ChenThese authors contributed equally., Ming, Yu, Le, Ren, Zhi-Hui, Wang, Yao-Yu, Guan, Zheng-Hui
Source:
Chemical communications 2017 v.53 no.46 pp. 6243-6246
ISSN:
1364-548X
Subject:
alkenes, carbon monoxide, catalysts, catalytic activity, chemical bonding, esters, palladium, regioselectivity, tautomerization
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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.
Agid:
6391604