Oxidative Cyclization Reactions: Controlling the Course of a Radical Cation-Derived Reaction with the Use of a Second Nucleophile
Autor: | Robert J. Perkins, Kevin D. Moeller, Alison Redden |
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Rok vydání: | 2013 |
Předmět: |
Free Radicals
Molecular Structure Bicyclic molecule Aryl Reactive intermediate Hydrocarbons Cyclic Ketene Stereoisomerism General Chemistry General Medicine Alkenes Radical cyclization Medicinal chemistry Enol Article Catalysis chemistry.chemical_compound chemistry Radical ion Nucleophile Cyclization Cations Electrochemistry Organic chemistry Oxidation-Reduction |
Zdroj: | Angewandte Chemie. 125:13103-13106 |
ISSN: | 0044-8249 |
DOI: | 10.1002/ange.201308739 |
Popis: | The oxidative generation of reactive radical cation intermediates can serve as a powerful tool for the construction of new ring systems.[1,2] For example, substrates with electronrich olefins can be oxidized to generate radical cations that trigger cyclizations with a variety of electron-rich groups.[3] Enol ethers, vinylsulfides, ketene derivatives, electron-rich aryl rings, and styrenes have all been oxidized to form radical cations, whereas enol ethers, allyl and vinylsilanes, aryl rings, styrenes, alcohols, amides, sulfonamides, and amines have all been used to trap the radical cation. The reactions have led to the synthesis of fused and bicyclic ring skeletons and are often compatible with the formation of tetrasubstituted carbons. In addition, they have served to help us gain a better understanding of radical cation intermediates.[4] |
Databáze: | OpenAIRE |
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