Synthesis of pentafluorobenzene-based NHC adducts and their catalytic activity in the microwave-assisted reactions of aldehydes

[Display omitted] •Synthesis of pentafluorobenzene-based NHC precursors.•NHC-catalyzed synthesis of hydroxymethyl ketones using MW irradiation.•Efficient synthesis of aliphatic hydroxymethyl ketones. N-Heterocyclic carbenes (NHCs) have been widely used in organometallic chemistry as ligands, as well...

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Bibliographic Details
Published in:Tetrahedron letters 2020-01, Vol.61 (4), p.151419, Article 151419
Main Authors: Papadaki, Evanthia, Magrioti, Victoria
Format: Article
Language:English
Subjects:
Green chemistry
Microwave irradiation
N-Heterocyclic carbenes
Organocatalysis
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Summary:[Display omitted] •Synthesis of pentafluorobenzene-based NHC precursors.•NHC-catalyzed synthesis of hydroxymethyl ketones using MW irradiation.•Efficient synthesis of aliphatic hydroxymethyl ketones. N-Heterocyclic carbenes (NHCs) have been widely used in organometallic chemistry as ligands, as well as standalone organocatalysts in various reactions, mostly using aromatic aldehydes as substrates. We have previously demonstrated the efficiency of azolium-2-carboxylate zwitterions in the hydroxymethylation of aldehydes, especially aliphatic aldehydes, under microwave irradiation. In the present work, we report a series of pentafluorobenzene-based NHC adducts and their efficiency in the hydroxymethylation and self-condensation of aliphatic and aromatic aldehydes using microwave irradiation. The free carbenes are released under the reaction conditions and 1,3-dimesityl-2-(perfluorophenyl)imidazolidine and 1,3-bis(2,6-dimethylphenyl)-2-(perfluorophenyl)imidazolidine proved to be the most potent precatalysts.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151419