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Ligand-free Ullmann-type Arylation of Oxazolidinones by Diaryliodonium Salts Full article

Journal Organic and Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539
Output data Year: 2023, Volume: 21, Number: 9, Pages: 1952-1957 Pages count : 6 DOI: 10.1039/d2ob02122f
Authors Podrezova Ekaterina V. 1 , Okhina Alina A. 2,3 , Rogachev Artem D. 2,3 , Baykov Sergey 4,1 , Kirschning Andreas 5 , Yusubov Mekhman 1 , Soldatova Natalia S. 1 , Postnikov Pavel S 6,1
Affiliations
1 Research School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, Tomsk 634034, Russia
2 N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, acad. Lavrentiev ave., 9, Novosibirsk 630090, Russia
3 Novosibirsk State University, Pirogov str., 2, Novosibirsk 630090, Russia
4 Institute of Chemistry, Saint Petersburg State University, Saint Petersburg 199034, Russia
5 Leibniz University Hannover, Schneiderberg 1B, 30167 Hannover, Germany
6 Department of Solid State Engineering, Institute of Chemical Technology, Prague 16628, Czech Republic

Abstract: The arylation of azaheterocycles can be considered as one of the most important processes for the preparation of various biologically active compounds. In the present work, we describe a method for the copper-catalyzed N-arylation of hindered oxazolidinones using diaryliodonium salts. The method succeeds in good to excellent yields for the arylation of 4-alkyloxazolidinones, including sterically hindered isopropyl- and tert-butyl-substituted. The efficiency of the method was demonstrated for a wide range of diaryliodonium salts – symmetric and unsymmetric as well as ortho-substituted derivatives. The developed approach will provide an important contribution in the development and preparation of novel drugs and bioactive molecules containing oxazolidinone moieties.
Cite: Podrezova E.V. , Okhina A.A. , Rogachev A.D. , Baykov S. , Kirschning A. , Yusubov M. , Soldatova N.S. , Postnikov P.S.
Ligand-free Ullmann-type Arylation of Oxazolidinones by Diaryliodonium Salts
Organic and Biomolecular Chemistry. 2023. V.21. N9. P.1952-1957. DOI: 10.1039/d2ob02122f WOS Scopus ANCAN PMID OpenAlex
Dates:
Submitted: Nov 22, 2022
Accepted: Feb 6, 2023
Published online: Feb 6, 2023
Published print: Mar 7, 2023
Identifiers:
Web of science: WOS:000931652900001
Scopus: 2-s2.0-85148677194
Chemical Abstracts: 2023:302508
Chemical Abstracts (print): 182:48133
PMID: 36757159
OpenAlex: W4319316443
Citing:
DB Citing
OpenAlex 4
Web of science 4
Scopus 3
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