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Heteroatom-Centred Radicals for the Synthesis of Heterocyclic Compounds

  • Fabrice Dénès
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 54)

Abstract

An overview of the synthetic methods allowing the preparation of heterocyclic structures based upon the use of heteroatom-centred radicals (R–X•) is presented here. The discussion will be limited to specific examples for which the heteroatom (X = SiR2, GeR2, SnR2, PR, NR, O, S, SO2, Se) is included in the heterocyclic structure itself during the cyclisation process leading to its formation. These include the cyclisation of heteroatom-centred radicals onto unsaturated partners such as alkenes, alkynes, arenes, ketones or nitriles and the formation of the heterocycle via a sequence involving remote functionalisation reactions leading to halogenated intermediates, followed by ionic cyclisation (e.g. Hofmann–Löffler–Freytag reaction), as well as cascade reactions terminating with an intramolecular homolytic substitution (SHi) at the heteroatom in the final step.

Keywords

Alkoxy radicals Germyl radicals Heteroatom-centred radicals Intramolecular homolytic substitution (SHi) Intramolecular hydrogen atom transfer (1,n-HAT) Nitrogen-centred radicals Phosphorus-centred radicals Radical cyclisation Selenyl radicals Silyl radicals Sulphonyl radicals Thiol–ene Thiol–yne Thiyl radicals 

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Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.CEISAM UMR CNRS 6230Université de NantesNantes, Cedex 3France

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