Issue 18, 2021

Diethylammonium iodide as catalyst for the metal-free synthesis of 5-aryl-2-oxazolidinones from aziridines and carbon dioxide

Abstract

The catalytic potential of ammonium halide salts was explored in the coupling reaction of a model aziridine with carbon dioxide, highlighting the superior activity of [NH2Et2]I. Then, working at room temperature, atmospheric CO2 pressure and in the absence of solvent, the [NH2Et2]I-catalyzed synthesis of a series of 5-aryl-2-oxazolidinones was accomplished in good to high yields and excellent selectivity, from 2-aryl-aziridines with N-methyl or N-ethyl groups. NMR studies and DFT calculations outlined the pivotal role of both the diethylammonium cation and the iodide anion. The proposed method represents a convenient choice for obtaining a limited number of valuable molecules for which more complex and more expensive catalytic systems have been reported even in recent years.

Graphical abstract: Diethylammonium iodide as catalyst for the metal-free synthesis of 5-aryl-2-oxazolidinones from aziridines and carbon dioxide

Supplementary files

Article information

Article type
Paper
Submitted
09 Mar 2021
Accepted
19 Apr 2021
First published
19 Apr 2021

Org. Biomol. Chem., 2021,19, 4152-4161

Diethylammonium iodide as catalyst for the metal-free synthesis of 5-aryl-2-oxazolidinones from aziridines and carbon dioxide

G. Bresciani, M. Bortoluzzi, G. Pampaloni and F. Marchetti, Org. Biomol. Chem., 2021, 19, 4152 DOI: 10.1039/D1OB00458A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements