期刊
TETRAHEDRON LETTERS
卷 61, 期 4, 页码 -出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2019.151419
关键词
Green chemistry; N-Heterocyclic carbenes; Microwave irradiation; Organocatalysis
资金
- Special Account for Research Grants of the National and Kapodistrian University of Athens (SARG/NKUA)
- Hellenic Foundation for Research and Innovation (HFRI)
- General Secretariat for Research and Technology (GSRT), under the HFRI PhD Fellowship grant [2286/14477]
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-dimethylphenyI)-2-(perfluorophenyl)imidazolidine proved to be the most potent precatalysts. (C) 2019 Elsevier Ltd. All rights reserved.
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