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| Allylpalladium(II) Chloride Dimer Basic information |
| Allylpalladium(II) Chloride Dimer Chemical Properties |
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 | NIST Chemistry Reference | [Pd(Cl)(C3H5)]2(12012-95-2) |
| Allylpalladium(II) Chloride Dimer Usage And Synthesis |
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 |
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Precatalyst for the enantioselective hydrosilylation of olefins.
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Precatalyst for asymmetric allylic alkylation and amination.
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Used as a palladium source for cross-coupling reactions.
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Can be used with Trost ligands.
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Catalyst for the carbostannylation of alkynes.
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Used as a precatalyst for "-arylation of aldehydes.
| 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. | 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.] |
| Allylpalladium(II) Chloride Dimer Preparation Products And Raw materials |
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