The chemistry of heteroarylphosphorus compounds. Part 15. Phosphorus-31 nuclear magnetic resonance studies of the donor properties of heteroarylphosphines towards selenium and platinum(II)

Allen, David W.; Taylor, Brian F.

doi:10.1039/dt9820000051

Cited by 311 publications

(173 citation statements)

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“…Se couplings reported previously for other phosphine selenides, [63,64] thus we conclude that all the diphosphines used in this study should have comparable electronic properties. However, a titrimetric study of the protonation of diphosphines 5-9 indicated that the basicity of the cycloalkyl diphosphines is significantly greater than that of ligand 5 ( Table 2, see also the Supporting Information).…”

mentioning

confidence: 61%

Phosphine Ligands in the Palladium‐Catalysed Methoxycarbonylation of Ethene: Insights into the Catalytic Cycle through an HP NMR Spectroscopic Study

Fuente

Waugh

Eastham

et al. 2010

Chemistry A European J

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Novel cis-1,2-bis(di-tert-butyl-phosphinomethyl) carbocyclic ligands 6-9 have been prepared and the corresponding palladium complexes [Pd(O(3)SCH(3))(L-L)][O(3)SCH(3)] (L-L=diphosphine) 32-35 synthesised and characterised by NMR spectroscopy and X-ray diffraction. These diphosphine ligands give very active catalysts for the palladium-catalysed methoxycarbonylation of ethene. The activity varies with the size of the carbocyclic backbone, ligands 7 and 9, containing four- and six-membered ring backbones giving more active systems. The acid used as co-catalyst has a strong influence on the activity, with excess trifluoroacetic acid affording the highest conversion, whereas excess methyl sulfonic acid inhibits the catalytic system. An in operando NMR spectroscopic mechanistic study has established the catalytic cycle and resting state of the catalyst under operating reaction conditions. Although the catalysis follows the hydride pathway, the resting state is shown to be the hydride precursor complex [Pd(O(3)SCH(3))(L-L)][O(3)SCH(3)], which demonstrates that an isolable/detectable hydride complex is not a prerequisite for this mechanism.

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mentioning

confidence: 61%

Phosphine Ligands in the Palladium‐Catalysed Methoxycarbonylation of Ethene: Insights into the Catalytic Cycle through an HP NMR Spectroscopic Study

Fuente

Waugh

Eastham

et al. 2010

Chemistry A European J

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“…[14] The magnitude of phosphane selenides derived from the reaction of a tertiary phosphane and selenium was shown to be much dependent upon the nature of the organic groups bound to phosphorus. [13,15] Electron-withdrawing groups on phosphorus will cause the coupling constant to increase whereas electron-donating groups and bulky groups will cause it to decrease.…”

Section: Steric and Electronic Features Of The M-tpptc Ligandmentioning

confidence: 99%

A Novel Water‐Soluble m‐TPPTC Ligand: Steric and Electronic Features –Recent Developments in Pd‐ and Rh‐Catalyzed CC Bond Formations

et al. 2004

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Abstract:The steric and electronic features of the novel water-soluble phosphane m-TPPTC have been determined using NMR, IR and UV-VIS spectroscopic methods and compared to the well-known sulfonated analogue TPPTS. The higher basicity of m-TPPTC compared to TPPTS had an influence (selectivity and efficiency) either on Pd-or Rh-catalyzed C À C bond formations reactions. The Sonogashira copper-free cross-couplings of aryl iodides and ortho-functionalized aryl iodides were efficiently performed using the carboxylated phosphane m-TPPTC leading to the alkynes in high yields. The Pd/m-TPPTC system was found to be efficiently recycled under mild biphasic conditions in the Sonogashira reaction.

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“…Unlike monoansa or diansa ferrocenophanes, that are invariably strained, the cobaltabisdicarbollide unit allows for unprecedented and relaxed confronting diansa sandwich complexes without 20 major perturbation of the original sandwich structure as seen at the structural section.…”

Section: Cyclic Voltammogram Studiesmentioning

confidence: 99%

Relaxed but Highly Compact Diansa Metallacyclophanes

et al. 2011

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The chemistry of heteroarylphosphorus compounds. Part 15. Phosphorus-31 nuclear magnetic resonance studies of the donor properties of heteroarylphosphines towards selenium and platinum(II)

Cited by 311 publications

References 0 publications

Phosphine Ligands in the Palladium‐Catalysed Methoxycarbonylation of Ethene: Insights into the Catalytic Cycle through an HP NMR Spectroscopic Study

Phosphine Ligands in the Palladium‐Catalysed Methoxycarbonylation of Ethene: Insights into the Catalytic Cycle through an HP NMR Spectroscopic Study

A Novel Water‐Soluble m‐TPPTC Ligand: Steric and Electronic Features –Recent Developments in Pd‐ and Rh‐Catalyzed CC Bond Formations

Relaxed but Highly Compact Diansa Metallacyclophanes

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