Four- and Sixfold Tandem-Domino Reactions Leading to Dimeric Tetrasubstituted Alkenes Suitable as Molecular Switches.
Four- and Sixfold Tandem-Domino Reactions Leading to Dimeric Tetrasubstituted Alkenes Suitable as Molecular Switches.
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DOI：
10.1002/anie.201503538
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发表时间：
2015-08
影响因子：
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通讯作者：
L. Tietze;Bernd Waldecker;D. Ganapathy;Christoph Eichhorst;T. Lenzer;K. Oum;S. Reichmann;D. Stalke
中科院分区：
文献类型：
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作者：
L. Tietze;Bernd Waldecker;D. Ganapathy;Christoph Eichhorst;T. Lenzer;K. Oum;S. Reichmann;D. Stalke
以底物1和4为原料，采用钯催化的四重串联多米诺反应（包括两步碳钯化和两步C-H-活化）合成了两种具有内螺旋手性的四取代烯烃3和6.一个六重串联多米诺骨牌反应也开发了包括Sonogashira反应。合成了20个具有不同取代模式的化合物，产率高达97%。通过X射线晶体学的结构解析证实了两个烯烃部分的螺旋手性。一些化合物的光物理研究表明，通过光控制其立体化学构型的变化显着的开关性能。
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.