Stereoselective synthesis of highly functionalized indanes and dibenzocycloheptadienes through complex radical cascade reactions
| Autor: | Noelia Fuentes, Estíbaliz Merino, Andrés García-Domínguez, Cristina Nevado, Wangqing Kong |
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| Přispěvatelé: | University of Zurich, Nevado, Cristina |
| Rok vydání: | 2014 |
| Předmět: |
10120 Department of Chemistry
Stereochemistry 1503 Catalysis Radical Indane 1600 General Chemistry General Medicine General Chemistry Ring (chemistry) Catalysis Styrene radical cascades aryl migration chemistry.chemical_compound alkene difunctionalization chemistry dibenzocycloheptadienes Cascade indanes Polymer chemistry 540 Chemistry Stereoselectivity |
| Zdroj: | Angewandte Chemie (International ed. in English). 54(8) |
| ISSN: | 1521-3773 |
| Popis: | Two highly stereoselective radical-mediated syntheses of densely functionalized indanes and dibenzocycloheptadienes from ortho-vinyl- and ortho-vinylaryl-substituted N-(arylsulfonyl)-acrylamides, respectively, are presented here. The chemoselective addition of in situ generated radicals (X(·)) onto the styrene moieties triggers an unprecedented reaction cascade, resulting in the formation of one new C-X bond and two new C-C bonds, a formal 1,4-aryl migration, and the extrusion of SO2 to generate an amidyl radical intermediate. This intermediate, upon H abstraction, leads to the observed 5- and 7-membered ring carbocyclic products, respectively, in a highly efficient manner. |
| Databáze: | OpenAIRE |
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