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Article Dans Une Revue European Journal of Organic Chemistry Année : 2017

Atom-Economic Catalytic Direct Substitution of N,O-Acetals with Simple Ketones

Résumé

A general and powerful catalytic protocol for the direct amidoalkylation of simple enolizable ketones is described, with use of the Lewis superacid Sn(NTf2)4 as a catalyst under thermal conditions. A complete and rational study directed towards the development of efficient conditions for the coupling of a wide range of reaction partner combinations, including the most recalcitrant ones, is presented. The synthetic potential of the reaction is demonstrated through the use of a large set of both carbonyl and N,O-acetalic substrates, providing the corresponding amidoalkylated ketones in 49–99 % yield, by using very low catalyst loadings (≤ 1 mol-%). © 2017 WILEY-VCH Verlag GmbH and Co. KGaA, Weinheim

Domaines

Chimie
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Dates et versions

hal-02413313 , version 1 (16-12-2019)

Identifiants

Citer

Bahria Touati, Abderrahman El Bouakher, Mohamed Salah Azizi, Catherine Taillier, Raja Ben Othman, et al.. Atom-Economic Catalytic Direct Substitution of N,O-Acetals with Simple Ketones. European Journal of Organic Chemistry, 2017, 2017 (30), pp.4445-4460. ⟨10.1002/ejoc.201700530⟩. ⟨hal-02413313⟩
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