title: Enolizable Carbonyls and N,O-Acetals: A Rational Approach for Room-Temperature Lewis Superacid-Catalyzed Direct α-Amidoalkylation of Ketones and Aldehydes.
abstract: An efficient catalytic room-temperature direct α-amidoalkylation of carbonyl donors, that is, ketones and aldehydes with unbiased N,O-acetals, is described. Sn(NTf2 )4 is an optimal catalyst to promote this challenging transformation at low loading and the reaction shows promising scope. A comprehensive and rational evaluation of this reaction has led to the establishment of an empirical scale of nucleophilic reactivity for a broad set of ketones that should be helpful in the synthetic design and development of carbonyl α-functionalization methods.
authors.affiliation: Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre, France.|Laboratoire d'Application de la Chimie aux Ressources et Substances Naturelles et à l'Environnement-, LACReSNE-Faculté des Sciences de Bizerte-, 7021, Bizerte, Université de Carthage, Tunisie.
authors.forename: Bahria
authors.initials: B
authors.lastname: Touati
authors.affiliation: Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre, France.
authors.forename: Abderrahman
authors.initials: A
authors.lastname: El Bouakher
authors.affiliation: Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre, France.
authors.forename: Catherine
authors.initials: C
authors.lastname: Taillier
authors.affiliation: Ecole supérieure des sciences et de technologie de Hammam Sousse, Rue Lamine Abassi, 4011H, Sousse, Tunisie.
authors.forename: Raja Ben
authors.initials: RB
authors.lastname: Othman
authors.affiliation: Laboratoire d'Application de la Chimie aux Ressources et Substances Naturelles et à l'Environnement-, LACReSNE-Faculté des Sciences de Bizerte-, 7021, Bizerte, Université de Carthage, Tunisie.
authors.forename: Malika
authors.initials: M
authors.lastname: Trabelsi-Ayadi
authors.affiliation: Institut de Chimie de Nice, UMR 7272, Université de Nice Sophia Antipolis, C.N.R.S., Parc Valrose, 06108, Nice cedex 2, France.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Antoniotti
authors.affiliation: Institut de Chimie de Nice, UMR 7272, Université de Nice Sophia Antipolis, C.N.R.S., Parc Valrose, 06108, Nice cedex 2, France.
authors.forename: Elisabet
authors.initials: E
authors.lastname: Duñach
authors.affiliation: Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre, France. vincent.dalla@univ-lehavre.fr.
authors.forename: Vincent
authors.identifier: http://orcid.org/0000-0001-9043-5996
authors.initials: V
authors.lastname: Dalla
keywords: Lewis acids; alkylation; enols; lactams; superacidic systems