Dmitry Tsvelikhovsky - Forcing a cis-Product by Matrix Imprinting: Heck Reaction Catalyzed by Palladium Acetate Entrapped within cis-Imprinted Sol-Gel Derived Silicates

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      Publication Details (including relevant citation   information):

      Dmitry Tsvelikhovsky,a Dikla Pessing,a David Avnir,a,* and   Jochanan Bluma,*

     

      Adv. Synth. Catal. 2008, 350, 2856 – 2858

     

      Institute of Chemistry, The Hebrew University, Jerusalem 91904,   Israel

      Fax: (+972)-2-651-3832; e-mail: jblum@chem.ch.huji.ac.il or   david@chem.ch.huji.ac.il Received: September 23, 2008; Published   online: December 8, 2008

      Abstract:

      While the Heck coupling of aryl bromides with styrenes by   palladium acetate entrapped within octylated silica sol-gel forms   almost entirely trans-stilbenes, the catalysis by the palladium   com- pound within the cis-pre-imprinted support gives stilbenes   that are substantially enriched by cis-ori- ented isomers.   Although the ceramic support is completely freed from the imprint   prior to the cou- pling process, cis-stilbenes are formed with   similar selectivities upon recycling of the catalyst systems for   at least four consecutive runs.

      Address (URL): http://onlinelibrary.wiley.com.libproxy.mit.edu/doi/10.1002/adsc.200800590/pdf