Selective, high-yield, linear dimerization of 1,3-butadiene catalyzed by dibromobis(triphenylphosphine)nickel and sodium tetrahydroborate and its polymer-bound nickel(0) analog

Pittman, Charles U.; Smith, Larry R.

doi:10.1021/ja00835a019

Cited by 60 publications

(2 citation statements)

References 3 publications

(5 reference statements)

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“…Reactions with Polymer-Bound Ligands: The ‘Three-Phase Test'. Further evidence for potential participation of Ni sol in coupling reactions catalyzed by Ni/C was garnered from a set of experiments based on a ‘three-phase test', − in our case using polymer-bound PPh 3 as ligand . Given that solid-supported PPh 3 should only interact with Ni sol outside the matrix (and not with Ni C ),21a other preconditions had to be established so that the derived data would be meaningful.…”

Section: Resultsmentioning

confidence: 99%

On the Nature of the ‘Heterogeneous' Catalyst: Nickel-on-Charcoal

et al. 2002

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Results from aromatic aminations and Kumada couplings, together with spectroscopic analyses (TEM, EDX, ICP-AES, React-IR), reveal that catalysis using nickel-on-charcoal (Ni/C) is most likely of a homogeneous rather than heterogeneous nature. In the course of a reaction with Ni/C, nickel bleed from the support was calculated to be as high as 78%. However, the existence of an equilibrium for this homogeneous species between nickel located inside vs outside the pore system of charcoal strongly favors the former, thus leaving only traces of metal detectable in solution. This accounts for virtually complete recovery of nickel on the charcoal following filtration of a reaction mixture and allows for recycling of the catalyst. TEM and EDX data were used to explain different reactivity profiles of Ni/C, which depended upon the method of reduction used to convert Ni(II)/C to Ni(0) as well as the level of nickel loading on the support.

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Section: Resultsmentioning

confidence: 99%

On the Nature of the ‘Heterogeneous' Catalyst: Nickel-on-Charcoal

et al. 2002

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“…In the field of phosphine-mediated organic chemistry, the use of polymer-bound phosphines has successfully been adapted to the conversion of alcohols to alkyl chlorides and, in Wittig − or Mitsunobu − reactions, to facilitate the separation of the products from phosphine oxides at the end of the reaction. Diphenylphosphino polystyrene resins have also been employed to generate polymer-bound iridium, , nickel, rhodium, − and ruthenium catalysts for use in hydrogenation, ,, alkene dimerization, and hydroformylation 12-14 reactions. Diphenylphosphinomethyl polystyrene resins have been used to complex palladium − and rhodium 11 for use as reusable catalysts in Suzuki 15 and hydrogenation 8,9,15 reactions, respectively.…”

Section: Introductionmentioning

confidence: 99%

Quantitative Determination of Loadings and Oxidation Products of Polystyrene-Bound Phosphines Using ³¹P MAS NMR

et al. 2003

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The use of (31)P magic angle spinning (MAS) NMR for the quantitative determination of resin loadings and the building up of oxidation products was investigated. Loadings of polystyrene-bound phosphines were evaluated via addition of triphenyl phosphate as reference compound. Results for a series of phosphines are consistent with those obtained from well-established analytical methods. The compounds were also investigated with (13)C MAS NMR, and the individual oxidation stabilities were monitored under oxygen atmosphere.

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Dibromobis(triphenylphosphine)nickel(II)

Luh¹,

Kuo²

2001

Encyclopedia of Reagents for Organic Synthesis

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Selective, high-yield, linear dimerization of 1,3-butadiene catalyzed by dibromobis(triphenylphosphine)nickel and sodium tetrahydroborate and its polymer-bound nickel(0) analog

Cited by 60 publications

References 3 publications

On the Nature of the ‘Heterogeneous' Catalyst: Nickel-on-Charcoal

On the Nature of the ‘Heterogeneous' Catalyst: Nickel-on-Charcoal

Quantitative Determination of Loadings and Oxidation Products of Polystyrene-Bound Phosphines Using ³¹P MAS NMR

Dibromobis(triphenylphosphine)nickel(II)

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Selective, high-yield, linear dimerization of 1,3-butadiene catalyzed by dibromobis(triphenylphosphine)nickel and sodium tetrahydroborate and its polymer-bound nickel(0) analog

Cited by 60 publications

References 3 publications

On the Nature of the ‘Heterogeneous' Catalyst: Nickel-on-Charcoal

On the Nature of the ‘Heterogeneous' Catalyst: Nickel-on-Charcoal

Quantitative Determination of Loadings and Oxidation Products of Polystyrene-Bound Phosphines Using 31P MAS NMR

Dibromobis(triphenylphosphine)nickel(II)

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Quantitative Determination of Loadings and Oxidation Products of Polystyrene-Bound Phosphines Using ³¹P MAS NMR