Enolizable Carbonyls and N,O-Acetals: A Rational Approach for Room-Temperature Lewis Superacid-Catalyzed Direct α-Amidoalkylation of Ketones and Aldehydes.
Bahria TouatiAbderrahman El BouakherCatherine TaillierRaja Ben OthmanMalika Trabelsi-AyadiSylvain AntoniottiElisabet DuñachVincent DallaPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (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.