1215178-29-2Relevant academic research and scientific papers
Enolizable Carbonyls and N,O-Acetals: A Rational Approach for Room-Temperature Lewis Superacid-Catalyzed Direct α-Amidoalkylation of Ketones and Aldehydes
Touati, Bahria,El Bouakher, Abderrahman,Taillier, Catherine,Othman, Raja Ben,Trabelsi-Ayadi, Malika,Antoniotti, Sylvain,Du?ach, Elisabet,Dalla, Vincent
, p. 6012 - 6022 (2016)
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.
Atom-Economic Catalytic Direct Substitution of N,O-Acetals with Simple Ketones
Touati, Bahria,El Bouakher, Abderrahman,Azizi, Mohamed Salah,Taillier, Catherine,Ben Othman, Raja,Trabelsi-Ayadi, Malika,Antoniotti, Sylvain,Du?ach, Elisabet,Dalla, Vincent
supporting information, p. 4445 - 4460 (2017/08/23)
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 direc
N-acyliminium ion chemistry: Highly efficient and versatile carbon-carbon bond formation by nucleophilic substitution of hydroxy groups catalyzed by Sn(NTf2)4
Othman, Raja Ben,Affani, Radouane,Tranchant, Marie-Jose,Antoniotti, Sylvain,Dalla, Vincent,Dunach, Elisabet
supporting information; experimental part, p. 776 - 780 (2010/04/24)
(Chemical Equation Presentation) Atom-economical: Unmodified hemiN,O-acetals are used in a catalytic, highly efficient α- amidoalkylation of a broad range of carbon-centered nucleophiles, including silicon-based components, active methylene derivatives, electron-rich arenes, and even simple ketones (see scheme). The reactions proceed in a highly efficient manner and typically require only 1 mol% of the Lewis super-acidic reagent Sn(NTf2)4 as the catalyst.
