Recyclable hybrid silica-based catalysts derived from Pd-NHC complexes for suzuki, heck and sonogashira reactions

Guadalupe Borja, Amàlia Monge-Marcet, Roser Pleixats, Teodor Parella, Xavier Cattoën, Michel Wong Chi Man

Research output: Contribution to journalArticleResearchpeer-review

66 Citations (Scopus)

Abstract

Two silylated Pd-NHC complexes were immobilized on hybrid silicas by sol-gel cocondensation with tetraethyl orthosilicate (TEOS) and performed well as recyclable catalysts towards the Heck, Suzuki, and Sonogashira coupling reactions. Remarkable conversion and recyclability were achieved in the Suzuki reaction with a challenging aryl chloride. No side products and no undesired homocoupling were observed in Suzuki or Heck reactions, which facilitates the final purification step for the cross-coupling products. High turnover numbers and turnover frequencies were found for copper- and phosphane-free Sonogashira reaction between p-bromoacetophenone and phenylacetylene. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Original languageEnglish
Pages (from-to)3625-3635
JournalEuropean Journal of Organic Chemistry
Issue number19
DOIs
Publication statusPublished - 1 Jul 2012

Keywords

  • C-C coupling
  • Carbenes
  • Cross-coupling
  • Green chemistry
  • Heterogeneous catalysis
  • Palladium
  • Sol-gel processes
  • Supported catalysts

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