Ligand-free Ullmann-type Arylation of Oxazolidinones by Diaryliodonium Salts | Sciact - CRIS-system of Boreskov Institute of Catalysis

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

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.

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

Submitted:	Nov 22, 2022
Accepted:	Feb 6, 2023
Published online:	Feb 6, 2023
Published print:	Mar 7, 2023

Web of science:	WOS:000931652900001
Scopus:	2-s2.0-85148677194
Chemical Abstracts:	2023:302508
Chemical Abstracts (print):	182:48133
PMID:	36757159
OpenAlex:	W4319316443

DB	Citing
OpenAlex	6
Web of science	7
Scopus	6