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Stereoselective synthesis of highly functionalized indanes and dibenzocycloheptadienes through complex radical cascade reactions


Kong, Wangqing; Fuentes, Noelia; García-Domínguez, Andres; Merino, Estíbaliz; Nevado, Cristina (2015). Stereoselective synthesis of highly functionalized indanes and dibenzocycloheptadienes through complex radical cascade reactions. Angewandte Chemie Internationale Edition, 54(8):2487-2491.

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.

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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:alkene difunctionalization aryl migration dibenzocycloheptadienes indanes radical cascades
Language:English
Date:2015
Deposited On:20 Nov 2015 11:31
Last Modified:31 May 2016 18:28
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:1433-7851
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1002/anie.201409659

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