Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 11-12, Pages 1993-2001Publisher
WILEY-BLACKWELL
DOI: 10.1002/adsc.201000028
Keywords
cross-coupling reactions; heterogeneous palladium catalysts; multi-component reaction; one-pot synthesis; stilbenes; Suzuki/Heck sequence
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Funding
- CNRS
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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/SiO(2)) catalyst with potassium phosphate monohydrate (K(3)PO(4)H(2)O) 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-methyl-pyrrolidone (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 he extremely robust despite the use of aerobic conditions and was successfully re-used over several cycles.
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