Email this article Microwave-promoted N-arylation of imidazole and amino acids in the presence of Cu2O and CuO in poly(ethylene glycol)
- Authors: Yakushev A.A.1,2,3, Averin A.D.1,4, Colacino E.2,3, Lamaty F.2,3, Beletskaya I.P.1,4
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Affiliations:
- Department of Chemistry, M. V. Lomonosov Moscow State University
- Max Mousseron Institute of Biomolecules, Montpellier University 2
- Institut des Biomolécules Max Mousseron (IBMM) UMR 5247, Université Montpellier 2
- A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
- Issue: Vol 65, No 5 (2016)
- Pages: 1243-1248
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/238086
- DOI: https://doi.org/10.1007/s11172-016-1442-8
- ID: 238086
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Abstract
Copper(I)-catalyzed N-arylation of imidazole with iodobenzene, its derivatives, and bromobenzene in poly(ethylene glycol) under microwave irradiation was studied. The influence of the following factors on the yield of arylation product was investigated: the nature of the source of copper and ligand, type of poly(ethylene glycol) (PEG) used, and substituents in iodoarene. An optimal catalytic system was selected: CuO/l-Hys/Cs2CO3/PEG-400, a possibility of recycling of copper-containing catalyst was demonstrated. N-Arylation of eight natural amino acids using catalysis with Cu2O/Cs2CO3/PEG-400 and microwave irradiation was studied, the dependence of the reaction results on temperature, duration of the process, and the ratio of the starting reagents was found. The highest yields of the target products were reached in the case of leucine, valine, and phenylalanine.
About the authors
A. A. Yakushev
Department of Chemistry, M. V. Lomonosov Moscow State University; Max Mousseron Institute of Biomolecules, Montpellier University 2; Institut des Biomolécules Max Mousseron (IBMM) UMR 5247, Université Montpellier 2
Email: beletska@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991; Montpellier; Montpellier
A. D. Averin
Department of Chemistry, M. V. Lomonosov Moscow State University; A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Email: beletska@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991; Korp. 4, 31 Leninsky prosp., Moscow, 119991
E. Colacino
Max Mousseron Institute of Biomolecules, Montpellier University 2; Institut des Biomolécules Max Mousseron (IBMM) UMR 5247, Université Montpellier 2
Email: beletska@org.chem.msu.ru
France, Montpellier; Montpellier
F. Lamaty
Max Mousseron Institute of Biomolecules, Montpellier University 2; Institut des Biomolécules Max Mousseron (IBMM) UMR 5247, Université Montpellier 2
Email: beletska@org.chem.msu.ru
France, Montpellier; Montpellier
I. P. Beletskaya
Department of Chemistry, M. V. Lomonosov Moscow State University; A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Author for correspondence.
Email: beletska@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991; Korp. 4, 31 Leninsky prosp., Moscow, 119991
