Dehydrative Cross-Coupling of 1-Phenylethanol Catalysed by Palladium Nanoparticles Formed in situ Under Acidic Conditions.

Jason E. Camp, Thomas W. Bousfield, Jay J. Dunsford, James Adams, Joshua Britton, Michael W. Fay, Athanasios. Angelis-Dimakis

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A dehydrative cross-coupling of 1-phenylethanol catalysed by sugar derived, in situ formed palladium(0) nanoparticles under acidic conditions is realised. The acidic conditions allow for use of alcohols as a feedstock in metal-mediated coupling reactions via their in situ dehydration and subsequent cross-coupling. Extensive analysis of the size and morphology of the palladium nanoparticles formed in situ showed that the zero-valent metal was surrounded by hydrophilic hydroxyl groups. EDX-TEM imaging studies using a prototype silicon drift detector provided insight into the problematic role of molecular oxygen in the system. This increased understanding of the catalyst deactivation allowed for the development of the cross-coupling methodology. A 250-12,000 fold increase in molar efficiency was observed when compared to related two-step protocols that use alternative feedstocks for the palladium-mediated synthesis of stilbenes. This work opens up a new research area in which the active catalyst is formed, stabilised and regenerated by a renewable sugar.

Original languageEnglish
Pages (from-to)3862-3874
Number of pages13
JournalSynthesis
Volume50
Issue number19
Early online date27 Aug 2018
DOIs
Publication statusE-pub ahead of print - 27 Aug 2018

Keywords

  • stilbene aryl alkene prepn regioselective
  • phenylethanol stilbene aryl iodide Mizoroki Heck coupling palladium catalyst

Cite this

Camp, J. E., Bousfield, T. W., Dunsford, J. J., Adams, J., Britton, J., Fay, M. W., & Angelis-Dimakis, A. (2018). Dehydrative Cross-Coupling of 1-Phenylethanol Catalysed by Palladium Nanoparticles Formed in situ Under Acidic Conditions. Synthesis, 50(19), 3862-3874. https://doi.org/10.1055/s-0037-1610246