Issue 17, 2024

Dearomative difunctionalization of arenes via highly selective radical relay reactions

Abstract

Dearomatization of arenes emerges as a reliable strategy for crafting intricate 3D polycyclic frameworks. Nonetheless, the development of an efficient method for dearomatization across diverse arenes remains a formidable challenge, particularly in the case of unactivated benzene. In this study, we present a facile dearomative difunctionalization approach for unactivated arenes through a highly selective radical relay reaction. The reaction operates under mild conditions, devoid of metals, photocatalysts, and additives. This method exhibits a broad substrate scope and exceptional functional group tolerance, successfully transforming various aromatics, including inert naphthalene and benzene rings, indoles, pyrroles, benzofuran, and thiophene. Bioactivity assessments reveal a significant inhibitory effect of the synthesized complex polycyclic frameworks on HCT 116 cancer cells, with subsequent mouse experiments providing compelling evidence of its feasibility.

Graphical abstract: Dearomative difunctionalization of arenes via highly selective radical relay reactions

Supplementary files

Article information

Article type
Research Article
Submitted
29 May 2024
Accepted
05 Jun 2024
First published
11 Jun 2024

Org. Chem. Front., 2024,11, 4654-4662

Dearomative difunctionalization of arenes via highly selective radical relay reactions

N. Lei, Q. Zhang, P. Tao, C. Lu, Q. Lei and K. Zheng, Org. Chem. Front., 2024, 11, 4654 DOI: 10.1039/D4QO00964A

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