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Title
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Pd(II) and Pt(II) complexes of α-keto stabilized sulfur ylide: Synthesis, structural, theoretical and catalytic activity studies
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Type
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JournalPaper
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Keywords
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Synthesis, Pd(II) and Pt(II) complexes, Sulfur ylide, X-ray characterization,Theoretical study, Suzuki-Miyaura reaction.
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Abstract
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Reaction of dimethyl sulfide with 2, 3ʹ-dibromoacetophenone led to formation of sulfonium salt [Me2SCH2C(O)C6H4-m-Br]Br (1). The resulted sulfonium salt was treated with NaOH and gave the α-keto stabilized sulfur ylide Me2SC(H)C(O)C6H4-m-Br (2). This ligand was reacted with [MCl2(cod)] (M = Pd, Pt; cod = 1,5-cyclooctadiene) to form the new cis- and trans- [MCl2(ylide)2] (M = Pd (cis- and trans-3), Pt (cis- and trans-4)) complexes. Characterization of the obtained compounds was performed by elemental analysis, IR, 1H and 13C NMR. Recrystallization of dichlorobis(ylide) palladium(II) and platinum(II) complexes from DMSO solution yielded the crystalline products, which X-ray diffraction data revealed that the both compounds were crystallized as cis-[MCl2(ylide)(DMSO)] (M = Pd (5), Pt (6)) complexes. Also, a theoretical study on structure and nature of the M–C bonding between the Y ligand (ylide) and [MCl2.DMSO] fragments in [YMCl2.DMSO] (M=Pd, Pt) complexes has been reported via NBO and energy-decomposition analysis (EDA). Furthermore, the palladium catalyzed Suzuki- Miyaura reaction of various aryl chlorides with arylboronic acids was performed. The resultsshowed that the Pd(II) complexes cis- and trans-3 catalyzed efficiently coupling reactions at low catalyst loading and short reaction time.
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Researchers
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Robert W. Gable (Not In First Six Researchers), (Fifth Researcher), Mehdi Bayat (Fourth Researcher), Asieh Sedghi (Third Researcher), (Second Researcher), seyyed javad seyyadzadeh sabounchei (First Researcher)
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