Issue 15, 2024

Direct access to pyrrole anhydrides via oxidative self-coupling of pyrrole carboxaldehydes

Abstract

An elegant synthesis of pyrrole-2-carboxylic acid anhydrides from pyrrole-2-carboxaldehydes using TBAI as a catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant is described herein. Unlike the previous reports wherein pyrrole-2-carboxylic acids were invariably used, we report here for first time the oxidative self-coupling of N-benzyl pyrrole-2-carboxaldehydes for the synthesis of 1-benzyl-1H-pyrrole-2-carboxylic anhydrides. In addition, a one-pot synthesis of novel pyrrole-2-carboxamides from pyrrole-2-carboxaldehydes is also reported. The mechanistic investigation supports a previously unexplored oxidative self-coupling of a pyrrole acyl radical, leading to the synthesis of a carboxylic anhydride.

Graphical abstract: Direct access to pyrrole anhydrides via oxidative self-coupling of pyrrole carboxaldehydes

Supplementary files

Article information

Article type
Paper
Submitted
10 Jan 2024
Accepted
10 Mar 2024
First published
27 Mar 2024

Org. Biomol. Chem., 2024,22, 3045-3052

Direct access to pyrrole anhydrides via oxidative self-coupling of pyrrole carboxaldehydes

S. Panday, T. Maity, P. Bhatti and J. K. Laha, Org. Biomol. Chem., 2024, 22, 3045 DOI: 10.1039/D4OB00052H

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