Four- and Sixfold Tandem-Domino Reactions Leading to Dimeric Tetrasubstituted Alkenes Suitable as Molecular Switches

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 s...

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Bibliographic Details
Published in:	Angewandte Chemie International Edition Vol. 54; no. 35; pp. 10317 - 10321
Main Authors:	Tietze, Lutz F., Waldecker, Bernd, Ganapathy, Dhandapani, Eichhorst, Christoph, Lenzer, Thomas, Oum, Kawon, Reichmann, Sven O., Stalke, Dietmar
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 24-08-2015 WILEY‐VCH Verlag Wiley Subscription Services, Inc
Edition:	International ed. in English
Subjects:	Alkenes Alkenes - chemistry Catalysis Chirality Crystallography Crystallography, X-Ray CH activation domino reactions Helical helical structures molecular devices Molecular Structure palladium Palladium - chemistry Polymers - chemistry Stereoisomerism Switches Switching Synthesis X-rays CH activation palladium molecular devices domino reactions helical structures
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Summary:	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. Highly efficient palladium‐catalyzed fourfold tandem‐domino reactions consisting of two carbopalladation and two CH‐activation steps were developed for the synthesis of two types of tetrasubstituted alkenes with intrinsic helical chirality. 20 different substrates were prepared with yields of up to 97 %. Photophysical investigations revealed light‐induced switching properties of the products.
Bibliography:	We thank the Bundesland Niedersachsen, the Volkswagen Foundation, and the Deutsche Forschungsgemeinschaft for their generous support. In addition, our gratitude goes to the staff of the mechanical workshop at the Department Chemistry-Biology, University of Siegen, for excellent technical assistance. Bundesland Niedersachsen Volkswagen Foundation Deutsche Forschungsgemeinschaft ark:/67375/WNG-1C4JM7Z0-C ArticleID:ANIE201503538 istex:F94130C4169402F517CB4F35210CD3695BB546BD We thank the Bundesland Niedersachsen, the Volkswagen Foundation, and the Deutsche Forschungsgemeinschaft for their generous support. In addition, our gratitude goes to the staff of the mechanical workshop at the Department Chemistry–Biology, University of Siegen, for excellent technical assistance. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201503538