Studies of reactions of o-xylylene-α,α′-dihalides with palladium complexes and the catalytic synthesis of 3-isochromanone

R. V H Jones, W. Edward Lindsell, Greg C. Paddon-Jones, Daniel D. Palmer, Peter N. Preston, Georgina M. Rosair, Alan J. Whitton

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Abstract

Homogeneous catalysis by palladium complexes with phosphorus(III) ligands of the carbonylation of o-xylylene dihalides in the presence of water to form 3-isochromanone has been studied. Triphenylphosphine was found to provide the most effective catalyst, and by-products and intermediates of systems containing this ligand have been investigated. 2-Indanone is one by-product but is unstable to decomposition under catalytic conditions. Excess PPh3 is necessary to prolong activity of the catalyst but is also transformed to bis-phosphonium compound [o-C6H4(CH2PPh3)2]X2 (X = Cl or Br); this quaternization has been investigated and the structure of the bromide salt determined by X-ray diffraction. An unstable oxidative addition product of Pd(PPh3)4 was detected as a probable intermediate and related to the previously reported but catalytically-inactive complex trans-Pd(o-CH2C6H4CH2Cl)Cl(PMe3)2, which has been structurally characterized by X-ray diffraction in this work. © 2006 Elsevier B.V. All rights reserved.

Original languageEnglish
Pages (from-to)2378-2385
Number of pages8
JournalJournal of Organometallic Chemistry
Volume691
Issue number11
DOIs
Publication statusPublished - 15 May 2006

Keywords

  • 3-Isochromanone
  • Carbonylation
  • o-Xylylene dihalides
  • Palladium
  • Phosphonium salt

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    Jones, R. V. H., Lindsell, W. E., Paddon-Jones, G. C., Palmer, D. D., Preston, P. N., Rosair, G. M., & Whitton, A. J. (2006). Studies of reactions of o-xylylene-α,α′-dihalides with palladium complexes and the catalytic synthesis of 3-isochromanone. Journal of Organometallic Chemistry, 691(11), 2378-2385. https://doi.org/10.1016/j.jorganchem.2006.01.029