Radical Brook rearrangement: past, present, and future

Abstract

The Brook rearrangement has emerged as one of the most pivotal transformations in organic chemistry, with broad applications spanning organic synthesis, drug design, and materials science. Since its discovery in the 1950s, the anion-mediated Brook rearrangement has been extensively studied, laying the groundwork for the development of numerous innovative reactions. In contrast, the radical Brook rearrangement has garnered comparatively less attention, primarily due to the challenges associated with the controlled generation of alkoxyl radicals under mild conditions. However, recent advancements in visible-light catalysis and transition-metal catalysis have positioned the radical Brook rearrangement as a promising alternative synthetic strategy in organic synthesis. Despite these developments, significant limitations and challenges remain, warranting further investigation. This review provides an overview of the radical Brook rearrangement, tracing its development from past to present, and offers perspectives on future directions in the field to inspire the creation of novel synthetic tools based on this transformation.

Graphical abstract: Radical Brook rearrangement: past, present, and future

Article information

Article type
Review Article
Submitted
18 Dec 2024
First published
21 Jan 2025

Chem. Soc. Rev., 2025, Advance Article

Radical Brook rearrangement: past, present, and future

Y. Zhang, G. Zhou, S. Liu and X. Shen, Chem. Soc. Rev., 2025, Advance Article , DOI: 10.1039/D4CS01275E

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