CuF<sub>2</sub>/DTBP-Catalyzed Chan-Lam Coupling of Oxazolidinones with Arylboronic Acid Pinacol Ester: Scope and Application

A new combination of CuF<sub>2</sub>/DTBP-catalyzed <i>N</i>-arylation of oxazolidinones, amides, amines, and azoles has been explored with arylboronic acid pinacol esters (arylBpin). This methodology has also been applied to the synthesis of oxazolidinone-based marketed drugs, including Rivaroxaban, Linezolid, Sutezolid, and Toloxatone. Mechanistic investigations using various spectroscopic techniques and DFT studies revealed the role of DTBP/MeOH in the catalytic process.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-04-25
DOI
https://doi.org/10.1021/acs.joc.5c00283
Citations
6
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
4.74

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article

CuF2/DTBP-Catalyzed Chan-Lam Coupling of Oxazolidinones with Arylboronic Acid Pinacol Ester: Scope and Application

Krishanu Mondal, Parthasarathi Das, Arunava Sengupta, Tanumay Roy et al.
6 citations
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
4.74
article

CuF2/DTBP-Catalyzed Chan-Lam Coupling of Oxazolidinones with Arylboronic Acid Pinacol Ester: Scope and Application

Krishanu Mondal, Parthasarathi Das, Arunava Sengupta, Tanumay Roy, Pallabi Halder
article en
6 citations

Abstract

A new combination of CuF<sub>2</sub>/DTBP-catalyzed <i>N</i>-arylation of oxazolidinones, amides, amines, and azoles has been explored with arylboronic acid pinacol esters (arylBpin). This methodology has also been applied to the synthesis of oxazolidinone-based marketed drugs, including Rivaroxaban, Linezolid, Sutezolid, and Toloxatone. Mechanistic investigations using various spectroscopic techniques and DFT studies revealed the role of DTBP/MeOH in the catalytic process.

The Journal of Organic ChemistryVol. 90(18)
Indian Institute of Technology Dhanbad (IN)
Indian Institute of Technology (Indian School of Mines), Dhanbad, Science and Engineering Research Board, Board of Research in Nuclear Sciences
Openalex Percentile: Top 5%
Fluorine in Organic Chemistry
4.74
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