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

Bahria Touati; Abderrahman El Bouakher; Mohamed Salah Azizi; Catherine Taillier; Raja Ben Othman; Malika Trabelsi-Ayadi; Sylvain Antoniotti; Elisabet Duñach; Vincent Dalla

doi:10.1002/ejoc.201700530

Journal articles

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

Bahria Touati ¹ Abderrahman El Bouakher ¹ Mohamed Salah Azizi ¹ Catherine Taillier ¹ Raja Ben Othman ² Malika Trabelsi-Ayadi ³ Sylvain Antoniotti ⁴ Elisabet Duñach ⁴ Vincent Dalla ¹

1 URCOM - Unité de Recherche en Chimie Organique et Macromoléculaire

2 ESSTHS - Ecole Supérieure des Sciences et de Technologie de Hammam Sousse

3 Université de Carthage - University of Carthage

4 ICN - Institut de Chimie de Nice

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

Keywords : O-acetals Tin N Amidoalkylation Enols Ketones Lewis acids

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Journal articles

Domain :

Chemical Sciences

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https://hal-normandie-univ.archives-ouvertes.fr/hal-02413313
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Submitted on : Monday, December 16, 2019 - 10:45:16 AM
Last modification on : Monday, October 12, 2020 - 10:28:49 AM

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

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

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