Dual-Functional Group Transfer Reagents for Dihalogenation Reactions

 

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Abstract

Functional group transfer reagents (FGTRs) represent a powerful strategy for introducing diverse functionalities into organic molecules. Herein, we describe the development and application of novel dual-functional group transfer reagents designed to facilitate efficient and selective vicinal dihalogenation of unsaturated hydrocarbons under mild photoredox catalytic conditions. Experimental investigations, coupled with density functional theory calculations, provide detailed mechanistic insights into the reaction, highlighting a unique radical-polar crossover mechanism involving radical ‘halogen dance’ and ionic addition of molecular dihalogens. The developed dual-FGTR approach showcases superior scalability, functional group tolerance, and practical applicability in a synthetic chemistry context.

1 Introduction

2 Reagent Design

3 Transfer Dihalogenation Span

4 Mechanistic Insights

5 Conclusion

Publication History

Received: 27 March 2025

Accepted after revision: 29 April 2025

Article published online:
01 July 2025

© 2025. Thieme. All rights reserved

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany

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