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Synlett 2022; 33(11): 1017-1028
DOI: 10.1055/a-1771-5037
DOI: 10.1055/a-1771-5037
account
Radical Heteroarylation of Alkenes and Alkanes via Heteroaryl Migration
The authors are grateful for the financial support from the National Natural Science Foundation of China (21971173, 22001185, and 22171201), the Natural Science Foundation of Jiangsu Province (BK20200852), the Natural Science Fund for Colleges and Universities in Jiangsu Province (20KJB150010), the Project of Scientific and Technological Infrastructure of Suzhou (SZS201905), and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).
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 functionalizationPublication History
Received: 18 January 2022
Accepted after revision: 14 February 2022
Accepted Manuscript online:
14 February 2022
Article published online:
14 March 2022
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