Hemilabile imino-phosphine palladium(II) complexes: Synthesis, molecular structure, and evaluation in Heck reactions

William M. Motswainyana, Martin O. Onani, Roger A. Lalancette, Paul K. Tarus

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

The ligands 2-(diphenylphosphino)benzyl-(2-thiophene)methylimine (V) and 2-(diphenylphosphino) benzyl-(2-thiophene)ethylimine (VI) were prepared from 2-(diphenylphosphino)benzaldehyde and thiophene amines with very good yields. An equimolar reaction of V and VI with either PdCl2(cod) (cod = cyclooctadiene) or PdClMe(cod) afforded palladium(II) complexes I-IV. The molecular structure of II was confirmed by X-ray crystallography. The coordination geometry around the palladium atom exhibited distorted square planar geometry at the palladium centre. Complexes I, II, and IV were evaluated as catalysts for Heck coupling reactions of iodobenzene with methyl acrylate under mild reaction conditions; 0.1 mole % catalyst, Et3N base, MeCN reflux for 8 h, 80 C; isolated yield on a 10 mmol scale with catalyst I (64 %), II (68 %), and IV (58 %). They all exhibited significant activities.

Original languageEnglish (US)
Pages (from-to)932-939
Number of pages8
JournalChemical Papers
Volume68
Issue number7
DOIs
StatePublished - Jul 2014

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Chemistry(all)
  • Chemical Engineering(all)
  • Industrial and Manufacturing Engineering
  • Materials Chemistry

Keywords

  • Heck reaction
  • Schiff-base molecular structures
  • imino-phosphine
  • palladium

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