TY - JOUR

T1 - Ligand-free Ullmann-type arylation of oxazolidinones by diaryliodonium salts

AU - Podrezova, Ekaterina V.

AU - Okhina, Alina A.

AU - Rogachev, Artem D.

AU - Baykov, Sergey V.

AU - Kirschning, Andreas

AU - Yusubov, Mekhman S.

AU - Soldatova, Natalia S.

AU - Postnikov, Pavel S.

N1 - Funding Information: This work represents an integration of two separate projects funded: the synthetic part were conducted under grant of the Council for Grants of the President of Russian Federation (project MK-337.2022.1.3), while the crystal engineering part was performed under “Mega-grant” project (no. 075-15-2021-585) of the Ministry of Science and Higher Education of the Russian Federation. N. S. and E. P., are grateful to the German Academic Exchange Service (DAAD) for the opportunity to internship with A. Kirschning. Authors are grateful the Center for X-ray Diffraction Studies and Center for Chemical Analysis and Materials Research (all belonging to Saint Petersburg State University) for the physicochemical studies. The authors greatly acknowledge the Laboratory of Physical-Chemical Analytical Methods of Tomsk State University for the NMR analyses and the Multi-Access Chemical Research Center SB RAS for spectral and analytical measurements.

PY - 2023/3/7

Y1 - 2023/3/7

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85148677194&partnerID=8YFLogxK

U2 - 10.1039/d2ob02122f

DO - 10.1039/d2ob02122f

M3 - Article

C2 - 36757159

AN - SCOPUS:85148677194

VL - 21

SP - 1952

EP - 1957

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 9

ER -