Four- and Sixfold Tandem-Domino Reactions Leading to Dimeric Tetrasubstituted Alkenes Suitable as Molecular Switches
2015 | journal article. A publication with affiliation to the University of Göttingen.
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Four- and Sixfold Tandem-Domino Reactions Leading to Dimeric Tetrasubstituted Alkenes Suitable as Molecular Switches
Tietze, L. F.; Waldecker, B.; Ganapathy, D.; Eichhorst, C.; Lenzer, T.; Oum, K. & Reichmann, S. O. et al. (2015)
Angewandte Chemie International Edition, 54(35) pp. 10317-10321. DOI: https://doi.org/10.1002/ange.201503538
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Details
- Authors
- Tietze, Lutz Friedjan; Waldecker, Bernd; Ganapathy, Dhandapani; Eichhorst, Christoph; Lenzer, Thomas; Oum, Kawon; Reichmann, Sven O.; Stalke, Dietmar
- Abstract
- A highly efficient palladium-catalyzed fourfold tandem-domino reaction consisting of two carbopalladation and two C-H-activation steps was developed for the synthesis of two types of tetrasubstituted alkenes 3 and 6 with intrinsic helical chirality starting from substrates 1 and 4, respectively. A sixfold tandem-domino reaction was also developed by including a Sonogashira reaction. 20 compounds with different substitution patterns were prepared with yields of up to 97%. Structure elucidation by X-ray crystallography confirmed helical chirality of the two alkene moieties. Photophysical investigations of some of the compounds showed pronounced switching properties through light-controlled changes of their stereochemical configuration.
- Issue Date
- 2015
- Status
- published
- Publisher
- Wiley-v C H Verlag Gmbh
- Journal
- Angewandte Chemie International Edition
- ISSN
- 1521-3773; 1433-7851
