12012-95-2 Usage
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
Different sources of media describe the Uses of 12012-95-2 differently. You can refer to the following data:
1. 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.
2. [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
Precatalyst for the enantioselective hydrosilylation of olefins.
Precatalyst for asymmetric allylic alkylation and amination.
Used as a palladium source for cross-coupling reactions.
Can be used with Trost ligands.
Catalyst for the carbostannylation of alkynes.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 12012-95-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,2,0,1 and 2 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 12012-95:
(7*1)+(6*2)+(5*0)+(4*1)+(3*2)+(2*9)+(1*5)=52
52 % 10 = 2
So 12012-95-2 is a valid CAS Registry Number.
InChI:InChI=1/2C3H3.2ClH.2Pd/c2*1-3-2;;;;/h2*1H,2H2;2*1H;;/q2*-3;;;;+2/r2C3H3.Cl2H2Pd.Pd/c3*1-3-2;/h2*1H,2H2;1-2H;/q2*-3;+2;
