Carbon-carbon and carbon-chlorine bond formation on reaction of iodine(III) reagents with the bis(alkynyl)palladium(II) motif, and structural chemistry of trans-Pd(CC-o-Tol)2(PMe2Ph)2] and trans-[PdCl(CC-o-Tol)(PMe2Ph)2] |
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Authors: | Manab Sharma Michael G. Gardiner Roderick C. Jones |
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Affiliation: | School of Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia |
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Abstract: | Trans-di(ortho-tolylethynyl)bis(dimethylphenylphosphine)palladium(II) reacts above −20 °C with the iodonium reagent IPhCl2 to give predominantly o-Tol-CC-Cl, above 15 °C with IPh2(OTf) (OTf = triflate) to give o-Tol-CC-Ph and (o-Tol-CC)2 in ca. 3:1 ratio, and above 10 °C with IPh(CCR)(OTf) (R = But, SiMe3) to give predominantly o-Tol-CC-CC-R and (o-Tol-CC)2. 31P NMR spectra provide evidence for detection of intermediates. The complexes trans-[Pd(CC-o-Tol)2(PMe2Ph)2] and trans-[PdCl(CC-o-Tol)(PMe2Ph)2] are obtained on reaction of trans-[PdCl2(PMe2Ph)2] with Li(CC-o-Tol) and o-Tol-CCH/Et3N, respectively, and have been characterised by X-ray crystallography. |
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Keywords: | Palladium Alkynyl Alkynylpalladium Oxidation Reductive elimination Carbon-carbon bond formation |
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