Radical Heteroarylation of Alkenes and Alkanes via Heteroaryl ­Migration

Yunlong Wei; Xinxin Wu; Chen Zhu

doi:10.1055/a-1771-5037

Synlett, Table of Contents

Synlett 2022; 33(11): 1017-1028
DOI: 10.1055/a-1771-5037

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Radical Heteroarylation of Alkenes and Alkanes via Heteroaryl Migration

Authors

Yunlong Wei

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, Jiangsu, P. R. of China
Xinxin Wu

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, Jiangsu, P. R. of China
Chen Zhu ∗

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, Jiangsu, P. R. of China

^bFrontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. of China

Abstract

All articles of this category

Abstract

Heteroarenes are important units in organic chemistry and are ubiquitous in natural products, pharmaceuticals, and numerous artificial molecules. Despite great efforts devoted to accessing heteroarenes, the development of new methods to efficiently produce heteroarenes remains a long-term interest. Recently, the strategy of radical-mediated heteroaryl migration has supplied a robust toolkit for the synthesis of a diversity of heteroaryl-containing compounds. This Account summarizes our recent achievements in this field and provides insight into the incorporation of heteroarenes into organic skeletons.

1 Introduction

2 Radical-Mediated Heteroarylation of Alkanes and Alkenes via Intramolecular Heteroaryl Migration

2.1 C(sp³)–H Heteroarylation via Intramolecular Heteroaryl Migration

2.2 Difunctionalization of Alkenes via Intramolecular Heteroaryl Migration

3 Intermolecular Difunctionalization of Alkenes via ‘Docking-Migration’ Strategy

3.1 Sulfone-Based Bifunctional Reagents for Difunctionalization of Alkenes by Docking Migration

3.2 Sulfone-Based Reagents for the Synthesis of N-Fused Heteroarenes by Docking Migration

3.3 Tertiary Alcohol Based Bifunctional Reagents for Difunctionalization of Alkenes by Docking Migration

3.4 Diaryl Ether Based Bifunctional Reagents for Difunctionalization of Alkenes by Docking Migration

3.5 Conclusion

Key words

heteroarylation - radical reaction - functional group migration - alkene difunctionalization - C–H functionalization

Full Text

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Radical Heteroarylation of Alkenes and Alkanes via Heteroaryl ­Migration

Authors

Radical Heteroarylation of Alkenes and Alkanes via Heteroaryl Migration