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Atom‐Economic Catalytic Direct Substitution of N,O‐Acetals with Simple Ketones
Author(s) -
Touati Bahria,
El Bouakher Abderrahman,
Azizi Mohamed Salah,
Taillier Catherine,
Ben Othman Raja,
TrabelsiAyadi Malika,
Antoniotti Sylvain,
Duñach Elisabet,
Dalla Vincent
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700530
Subject(s) - superacid , chemistry , catalysis , yield (engineering) , lewis acids and bases , atom (system on chip) , simple (philosophy) , lewis acid catalysis , substitution (logic) , organic chemistry , combinatorial chemistry , computational chemistry , thermodynamics , philosophy , epistemology , computer science , programming language , embedded system , physics
A general and powerful catalytic protocol for the direct amidoalkylation of simple enolizable ketones is described, with use of the Lewis superacid Sn(NTf 2 ) 4 as a catalyst under thermal conditions. A complete and rational study directed towards the development of efficient conditions for the coupling of a wide range of reaction partner combinations, including the most recalcitrant ones, is presented. The synthetic potential of the reaction is demonstrated through the use of a large set of both carbonyl and N,O‐acetalic substrates, providing the corresponding amidoalkylated ketones in 49–99 % yield, by using very low catalyst loadings (≤ 1 mol‐%).