Silica-supported imine palladacycles - recyclable catalysts for the Suzuki reaction?

R B Bedford, C S J Cazin, M B Hursthouse, M E Light, K J Pike, S Wimperis

Research output: Contribution to journalArticlepeer-review

116 Citations (Scopus)

Abstract

Silica-supported, imine-based palladacyclic catalysts have been synthesised and the crystal structure of complex 9, the triphenylphosphine adduct of the pre-supported precursor complex 8, has been determined. The solid-supported catalysts show considerably lower activity in the Suzuki reaction than their homogeneous counterparts. Poor recyclability of the silica-immobilised catalysts and the presence of active catalysts in solution indicate that imine-based palladacyclic catalysts are unstable with respect to liberation of zero-valent palladium species. Whilst the solid-supported complexes are not useful as catalysts, they do function as excellent mechanistic probes. Studies on model complexes give further information on the processes that cause the liberation of zero-valent species not only from the solid-supported catalysts, but also from homogeneous systems. In all cases it appears that a reductive-elimination event occurs to generate the active catalyst. (C) 2001 Published by Elsevier Science B.V.

Original languageEnglish
Pages (from-to)173-181
Number of pages9
JournalJournal of Organometallic Chemistry
Volume633
Issue number1-2
Publication statusPublished - 7 Sept 2001

Keywords

  • Suzuki reaction
  • palladacycles
  • catalysis
  • silica supported
  • COUPLING REACTIONS
  • HECK REACTION
  • OXIDATIVE ADDITION
  • MECHANISM
  • PHOSPHINE
  • COMPLEX
  • BONDS

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