Microwave-assisted synthesis of hydroxymethyl ketones using azolium-2-carboxylate zwitterions as catalyst precursors

Papadaki, Evanthia; Delaude, Lionel; Magrioti, Victoria

doi:10.1016/j.tet.2017.11.024

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Microwave-assisted synthesis of hydroxymethyl ketones using azolium-2-carboxylate zwitterions as catalyst precursors

Papadaki, Evanthia; Delaude, Lionel; Magrioti, Victoria

2017 • In Tetrahedron, 73 (52), p. 7295-7300

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https://hdl.handle.net/2268/216913

DOI
10.1016/j.tet.2017.11.024

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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 :

Issue :

Pages :

7295-7300

Peer reviewed :

Peer Reviewed verified by ORBi

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since 12 December 2017

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