Header

UZH-Logo

Maintenance Infos

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.

Statistics

Citations

Dimensions.ai Metrics
60 citations in Web of Science®
64 citations in Scopus®
101 citations in Microsoft Academic
Google Scholar™

Altmetrics

Downloads

1 download since deposited on 20 Nov 2015
0 downloads since 12 months
Detailed statistics

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:14 Feb 2018 09:43
Publisher:Wiley-VCH Verlag
ISSN:1433-7851
OA Status:Closed
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1002/anie.201409659

Download