Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 2016

Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues

Résumé

The electronic effects governing the N-arylation of pyrrolidone were investigated. The generalization of our preliminary findings on a copper(I)-catalyzed Csp2-N coupling process was first improved with a wide variety of aryl and heteroaryl halides and methyl pyroglutamate. The optimized protocol was further extended to pyrrolidin-2-ones substituted at the C5-position with an aryl group bearing an electron-donating or electron-withdrawing group as well as to some of their substituted enaminoester vinylogues. The impact of substituents at the N- and C5-position on these coupling processes seemed to be pivotal for determining both the reaction profiles and yields.

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Dates et versions

hal-01688130 , version 1 (19-01-2018)

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Citer

Davy Baudelet, Adam Daïch, Benoît Rigo, Emmanuelle Lipka, Philippe Gautret, et al.. Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues. Synthesis: Journal of Synthetic Organic Chemistry, 2016, Synthesis (Germany), 48 (1414), pp.2226-2244. ⟨10.1055/s-0035-1561415⟩. ⟨hal-01688130⟩
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