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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. Magic Lewis superacid A room-temperature catalytic direct α-amidoalkylation reaction of ketones and aldehydes that operates via N-acyliminium ions generated in situ is reported (see scheme). This reaction is efficiently catalyzed by 0.5-2 mol % of the Lewis superacid Sn(NTf2)4 and exhibits a large scope. An evaluation of this Mannich coupling led to the establishment of a reactivity scale of enolizable ketones. © 2016 WILEY-VCH Verlag GmbH and Co. KGaA, Weinheim.
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Submitted on : Monday, December 16, 2019 - 10:45:20 AM
Last modification on : Sunday, May 1, 2022 - 3:16:46 AM

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Bahria Touati, Abderrahman El Bouakher, Catherine Taillier, Raja Ben Othman, Malika Trabelsi-Ayadi, et al.. Enolizable Carbonyls and N,O-Acetals A Rational Approach for Room-Temperature Lewis Superacid-Catalyzed Direct α-Amidoalkylation of Ketones and Aldehydes. Chemistry - A European Journal, Wiley-VCH Verlag, 2016, 22 (17), pp.6012-6022. ⟨10.1002/chem.201504772⟩. ⟨hal-02413315⟩

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