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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 | | InChI | InChI=1S/2C3H2.2ClH.2Pd/c2*1-3-2;;;;/h2*1-2H;2*1H;;/q2*-1;;;2*+2/p-2 | | InChIKey | GSVMTGORPBRYQY-UHFFFAOYSA-L | | SMILES | [Pd+2]123(C=C1[CH-]2)[Cl-][Pd+2]12(C=C1[CH-]2)[Cl-]3 | | NIST Chemistry Reference | [Pd(Cl)(C3H5)]2(12012-95-2) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-40 | | Safety Statements | 26-36-36/37 | | WGK Germany | 3 | | RTECS | RT3510000 | | F | 1-10 | | TSCA | No | | HS Code | 28439090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Skin Irrit. 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 | 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. | | 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 | | 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. | | 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.] |
| | Allylpalladium(II) Chloride Dimer Preparation Products And Raw materials |
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