Radical Heteroarylation of Alkenes and Alkanes via Heteroaryl ­Migration

Abstract

AbstractHeteroarenes 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 Introduction2 Radical-Mediated Heteroarylation of Alkanes and Alkenes via Intramolecular Heteroaryl Migration2.1 C(sp3)–H Heteroarylation via Intramolecular Heteroaryl Migration2.2 Difunctionalization of Alkenes via Intramolecular Heteroaryl Migration3 Intermolecular Difunctionalization of Alkenes via ‘Docking-Migration’ Strategy3.1 Sulfone-Based Bifunctional Reagents for Difunctionalization of Alkenes by Docking Migration3.2 Sulfone-Based Reagents for the Synthesis of N-Fused Heteroarenes by Docking Migration3.3 Tertiary Alcohol Based Bifunctional Reagents for Difunctionalization of Alkenes by Docking Migration3.4 Diaryl Ether Based Bifunctional Reagents for Difunctionalization of Alkenes by Docking Migration3.5 Conclusion