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- Title
Stereoselective Synthesis of Highly Functionalized Indanes and Dibenzocycloheptadienes through Complex Radical Cascade Reactions.
- Authors
Kong, Wangqing; Fuentes, Noelia; García-Domínguez, Andres; Merino, Estíbaliz; Nevado, Cristina
- Abstract
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 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 H abstraction, leads to the observed 5- and 7-membered ring carbocyclic products, respectively, in a highly efficient manner.
- Subjects
BINARY operations; BENZENE; EXTREMISTS; STYRENE; ARITHMETIC
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 8, p2517
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201409659