Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 8, Pages 2487-2491Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409659
Keywords
alkene difunctionalization; aryl migration; dibenzocycloheptadienes; indanes; radical cascades
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Funding
- European Research Council (ERC) [307948]
- University of Granada
- Swiss National Science Foundation
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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 insitu generated radicals (X-.) onto the styrene moieties triggers an unprecedented reaction cascade, resulting in the formation of one new CX bond and two new CC bonds, a formal 1,4-aryl migration, and the extrusion of SO2 to generate an amidyl radical intermediate. This intermediate, upon Habstraction, leads to the observed 5- and 7-membered ring carbocyclic products, respectively, in a highly efficient manner.
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