3240-26-4Relevant academic research and scientific papers
One-pot Suzuki/Heck sequence for the synthesis of (E)-stilbenes featuring a recyclable silica-supported palladium catalyst via a multi-component reaction in 1,3-propanediol
Joucla, Lionel,Cusati, Giuseppe,Pinel, Catherine,Djakovitch, Laurent
scheme or table, p. 1993 - 2001 (2010/10/20)
The synthesis of (E)-stilbenes was performed following a one-pot Suzuki/Heck sequence through the use of potassium vinyltrifluoroborate. The combination of heterogeneous palladium/silica (Pd/SiO2) catalyst with potassium phosphate monohydrate (K3PO4?H 2O) as base resulted in useful to good isolated yields regardless of the ortho-, meta- or para-substitution of the aryl halides employed. In a sustainable approach, we found that bio-sourced 1,3- propanediol could advantageously replace N-methylpyrrolidone (NMP) as similar yields were obtained. Moreover, the reactivity gap between aryl iodides and bromides resulting from the use of 1,3-propanediol allowed an efficient multi-component approach toward the synthesis of (E)-stilbenes. Furthermore, this heterogeneous catalyst was found to be extremely robust despite the use of aerobic conditions and was successfully re-used over several cycles.
