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

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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.

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Authors and Affiliations

  1. Chemistry Department, University of the Western Cape, Private Bag X17, 7535, Bellville, South Africa

    William M. Motswainyana & Martin O. Onani

  2. Carl A. Olson Memorial Laboratories, Department of Chemistry, Rutgers University, Newark, NJ, 07102, USA

    Roger A. Lalancette

  3. Department of Chemistry and Biochemistry, University of Eldoret, P.O. Box 1125-30100, Eldoret, Kenya

    Paul K. Tarus

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  1. William M. Motswainyana
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  2. Martin O. Onani
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  3. Roger A. Lalancette
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  4. Paul K. Tarus
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Correspondence to Martin O. Onani.

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Motswainyana, W.M., Onani, M.O., Lalancette, R.A. et al. Hemilabile imino-phosphine palladium(II) complexes: synthesis, molecular structure, and evaluation in Heck reactions. Chem. Pap. 68, 932–939 (2014). https://doi.org/10.2478/s11696-013-0530-6

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  • DOI: https://doi.org/10.2478/s11696-013-0530-6

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