title: Stereoselective synthesis of highly functionalized indanes and dibenzocycloheptadienes through complex radical cascade reactions.
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 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.
authors.affiliation: Department of Chemistry, University of Zürich, Winterthurerstrasse 190, 8057 Zürich (Switzerland).
authors.forename: Wangqing
authors.initials: W
authors.lastname: Kong
authors.forename: Noelia
authors.initials: N
authors.lastname: Fuentes
authors.forename: Andres
authors.initials: A
authors.lastname: García-Domínguez
authors.forename: Estíbaliz
authors.initials: E
authors.lastname: Merino
authors.forename: Cristina
authors.initials: C
authors.lastname: Nevado
keywords: alkene difunctionalization; aryl migration; dibenzocycloheptadienes; indanes; radical cascades