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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
Author(s) -
Touati Bahria,
El Bouakher Abderrahman,
Taillier Catherine,
Othman Raja Ben,
TrabelsiAyadi Malika,
Antoniotti Sylvain,
Duñach Elisabet,
Dalla Vincent
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504772
Subject(s) - superacid , catalysis , lewis acids and bases , chemistry , organic chemistry , medicinal chemistry
An efficient catalytic room‐temperature direct α‐amidoalkylation of carbonyl donors, that is, ketones and aldehydes with unbiased N , O ‐acetals, is described. Sn(NTf 2 ) 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.