Journal article
Stereoselective synthesis of highly functionalized indanes and dibenzocycloheptadienes through complex radical cascade reactions.
- Kong W Department of Chemistry, University of Zürich, Winterthurerstrasse 190, 8057 Zürich (Switzerland).
- Fuentes N
- García-Domínguez A
- Merino E
- Nevado C
- 2015-01-20
Published in:
- Angewandte Chemie (International ed. in English). - 2015
English
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.
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1002/anie.201409659
- PMID 25597296
- Persistent URL
- https://sonar.rero.ch/global/documents/35651
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