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Radical Brook rearrangement: past, present, and future.
Yunxiao Zhang1, Gang Zhou1, Shanshan Liu1
1The Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, 430072, China. xiaoshen@whu.edu.cn.
Chemical Society Reviews
|January 21, 2025
Summary
The radical Brook rearrangement offers a promising synthetic strategy in organic chemistry, building on decades of anion-mediated research. Recent catalytic advances enable milder conditions, but challenges remain for broader application.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- The Brook rearrangement is a key transformation in organic synthesis, with anion-mediated versions extensively studied since the 1950s.
- The radical Brook rearrangement has received less attention due to difficulties in generating alkoxyl radicals under mild conditions.
Purpose of the Study:
- To provide a comprehensive overview of the radical Brook rearrangement.
- To highlight recent advancements and future perspectives in this area of organic synthesis.
Main Methods:
- Review of existing literature on the Brook rearrangement, focusing on radical pathways.
- Analysis of recent developments in visible-light and transition-metal catalysis for radical generation.
Main Results:
- Visible-light and transition-metal catalysis are emerging as viable methods for the radical Brook rearrangement.
- Despite progress, significant challenges and limitations persist in controlled radical generation and application.
Conclusions:
- The radical Brook rearrangement presents a promising, albeit challenging, synthetic strategy.
- Further research is needed to overcome current limitations and develop novel synthetic tools based on this transformation.
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