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Allylpalladium(II) Chloride Dimer

Allylpalladium(II) Chloride Dimer Structure
Allylpalladium(II) Chloride Dimer
  • CAS No.12012-95-2
  • Chemical Name:Allylpalladium(II) Chloride Dimer
  • CBNumber:CB4156701
  • Molecular Formula:C6H10Cl2Pd2
  • Formula Weight:365.89
  • MOL File:12012-95-2.mol
Allylpalladium(II) Chloride Dimer Property
  • Melting point 120°C (dec.)
  • storage temp. 2-8°C
  • form Crystals or Crystalline Powder
  • color Yellow to green-yellow
  • Water Solubility decomposes
  • Sensitive Air Sensitive
  • BRN 4124623
  • EWG's Food Scores 1
  • NIST Chemistry Reference [Pd(Cl)(C3H5)]2(12012-95-2)
  • UNSPSC Code 12352200
  • NACRES NA.22
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H315
  • Precautionary statements P264-P280-P302+P352-P332+P313-P362+P364
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  • Product name : Allylpalladium(II) chloride dimer
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Allylpalladium(II) Chloride Dimer Chemical Properties,Usage,Production

  • Chemical Properties Allylpalladium(II) chloride dimer is a yellow powder with the formula [(η3-C3H5)PdCl]2. This compound is an important catalyst used in organic synthesis. It is one of the most widely used transition metal allyl complexes.
  • Uses [Pd(allyl)Cl]2 can be used as a catalyst:
    For the silylation of organobromides.
    To synthesize α-aryl carbonyl compounds by coupling reaction between aldehydes and aryl halides.
    To prepare various arylthiophene derivatives by cross-coupling reaction with aryl halides via C-H functionalization.
    Application Guide for Palladium Catalyzed Cross-Coupling Reactions
    ChemDose: Convenient Dosing of Catalysts and Reagents
  • Uses Allylpalladium(II) chloride dimer is used as an important catalyst in Heck reaction. It reacts with cyclopentadienyl anion to give cyclopentadienyl allyl palladium. It acts as a precatalyst for asymmetric and cross-coupling catalysis. Further, it is used in the preparation of 1,4-diallyl-1,2-dihydroisoquinolines. It is also employed as a catalyst for greener Buchwald-Hartwig coupling reaction and involved in the synthesis of cationic palladium catalysts. In addition, it takes part in preparation of -heterocyclic carbene-palladium-eta3-allyl chloride complex, which is an efficient catalyst for the Suzuki-Miyaura cross-coupling reactions in synthetic chemistry.
  • Preparation Allylpalladium(II) chloride dimer is prepared by purging carbon monoxide through a methanolic aqueous solution of palladium(II) chloride, sodium chloride, and allyl chloride.
    2Na2PdCl4 + 2 CH2=CHCH2Cl + 2 CO + 2 H2O → (C3H5)2Pd2Cl2 + 4 NaCl + 2 CO2 + 4 HCl
  • Reactions
    1. Precatalyst for the enantioselective hydrosilylation of olefins.
    2. Precatalyst for asymmetric allylic alkylation and amination.
    3. Used as a palladium source for cross-coupling reactions.
    4. Can be used with Trost ligands.
    5. Catalyst for the carbostannylation of alkynes.
    6. Used as a precatalyst for "-arylation of aldehydes.
    Reactions of 12012-95-2
  • General Description Allylpalladium(II) chloride dimer is employed as catalyst in Heck reaction. It also participates as catalyst in the tandem nucleophilic allylation-alkoxyallylation reaction of the alkynylaldehydes with allyl chloride and allyltributylstannane.
  • reaction suitability core: palladium
    reaction type: Cross Couplings
    reagent type: catalyst
    reaction type: C-H Activation
  • Purification Methods It crystallises from benzene and is soluble in MeOH, Et2O and CHCl3. [Hüttel et al. Chem Ber 94 766 1961, Dent et al. J Chem Soc 1585 1964, Armstrong J Org Chem 31 618 1966.]
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Allylpalladium(II) Chloride Dimer Spectrum
12012-95-2, Allylpalladium(II) Chloride DimerRelated Search:
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