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

Abstract : 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
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Contributor : Vincent Loisel Connect in order to contact the contributor
Submitted on : Monday, December 16, 2019 - 10:45:16 AM
Last modification on : Sunday, May 1, 2022 - 3:16:46 AM



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, Wiley-VCH Verlag, 2017, 2017 (30), pp.4445-4460. ⟨10.1002/ejoc.201700530⟩. ⟨hal-02413313⟩



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