Issue 37, 2024

Nitrogen-to-functionalized carbon atom transmutation of pyridine

Abstract

The targeted and selective replacement of a single atom in an aromatic system represents a powerful strategy for the rapid interconversion of molecular scaffolds. Herein, we report a pyridine-to-benzene transformation via nitrogen-to-carbon skeletal editing. This approach proceeds via a sequence of pyridine ring-opening, imine hydrolysis, olefination, electrocyclization, and aromatization to achieve the desired transmutation. The most notable features of this transformation are the ability to directly install a wide variety of versatile functional groups in the benzene scaffolding, including ester, ketone, amide, nitrile, and phosphate ester fragments, as well as the inclusion of meta-substituted pyridines which have thus far been elusive for related strategies.

Graphical abstract: Nitrogen-to-functionalized carbon atom transmutation of pyridine

Supplementary files

Article information

Article type
Edge Article
Submitted
04 Jul 2024
Accepted
25 Aug 2024
First published
26 Aug 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2024,15, 15205-15211

Nitrogen-to-functionalized carbon atom transmutation of pyridine

F. Wu, M. Lenz, A. Suresh, A. R. Gogoi, J. L. Tyler, C. G. Daniliuc, O. Gutierrez and F. Glorius, Chem. Sci., 2024, 15, 15205 DOI: 10.1039/D4SC04413D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements