Article (Scientific journals)
Microwave-assisted synthesis of hydroxymethyl ketones using azolium-2-carboxylate zwitterions as catalyst precursors
Papadaki, Evanthia; Delaude, Lionel; Magrioti, Victoria
2017In Tetrahedron, 73 (52), p. 7295-7300
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Keywords :
Green chemistry; Hydroxymethyl ketones; Microwave irradiation; N-Heterocyclic carbenes; Organocatalysis; Article
Abstract :
[en] Following an initial screening of six common imidazolium, imidazolinium, and dithiolium salts in the presence of a base, 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IDip) and 1,3-dimesitylimidazolin-2-ylidene (SIMes) were identified as promising organocatalysts for the microwave-assisted synthesis of hydroxymethyl ketones from aldehydes and paraformaldehyde. The azolium-2-carboxylate zwitterions IDip·CO2 and SIMes·CO2 were then tested as single-component N-heterocyclic carbene (NHC) precursors in the hydroxymethylation of heptanal and benzaldehyde. The latter adduct was an efficient precatalyst for the two reactions. It was successfully applied to a broad range of aliphatic and aromatic substrates (14 examples, 10–97% yields).
Disciplines :
Chemistry
Author, co-author :
Papadaki, Evanthia;  Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, Athens, Greece
Delaude, Lionel  ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie organométallique et catalyse homogène
Magrioti, Victoria;  Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, Athens, Greece
Language :
English
Title :
Microwave-assisted synthesis of hydroxymethyl ketones using azolium-2-carboxylate zwitterions as catalyst precursors
Publication date :
2017
Journal title :
Tetrahedron
ISSN :
0040-4020
Publisher :
Elsevier Ltd
Volume :
73
Issue :
52
Pages :
7295-7300
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 12 December 2017

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