CAS 12012-95-2 Allylpalladium(II) chloride dimer

Synonyms

Di-mu-chlorodi-pi-allyldipalladium; NSC 151255; Bis(pi-allylpalladium chloride) (VAN); MFCD00044874 (95%); Bis(mu-chloro)bis(eta3-2-propenyl)dipalladium; AK327212; 12012-95-2; Palladium, di-pi-allyldi-mu-chlorodi- (8CI); Bis((eta3-allyl)(chloro)palladium); SC10406;

IUPAC Name

chloropalladium(1+);prop-1-ene;

Molecular Weight

365.886g/mol

Molecular Formula

C6H10Cl2Pd2;

Canonical SMILES

[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+];

InChI

InChI=1S/2C3H5.2ClH.2Pd/c2*1-3-2;;;;/h2*3H,1-2H2;2*1H;;/q2*-1;;;2*+2/p-2;

InChI Key

PENAXHPKEVTBLF-UHFFFAOYSA-L;

Storage

2-8°C

Complexity

14.4

Covalently-Bonded Unit Count

EC Number

234-579-8

Exact Mass

365.823g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

363.823g/mol

Topological Polar Surface Area

0A^2

Application

Allylpalladium(II) chloride dimer, a yellow powder with the formula [(η3-C3H5)PdCl]2, serves as a pivotal catalyst in organic synthesis, notably recognized for its role in various transition metal allyl complex reactions. It is extensively used in the Heck reaction, facilitating the formation of cyclopentadienyl allyl palladium when reacting with cyclopentadienyl anion. This compound acts as a precatalyst in numerous processes, including asymmetric and cross-coupling catalysis, contributing to the synthesis of 1,4-diallyl-1,2-dihydroisoquinolines and enabling greener Buchwald-Hartwig coupling reactions. Additionally, it plays a key role in the formation of cationic palladium catalysts and the preparation of heterocyclic carbene-palladium-η3-allyl chloride complexes, utilized in efficient Suzuki-Miyaura cross-coupling reactions. As a catalyst, it is instrumental in the silylation of organobromides, the synthesis of α-aryl carbonyl compounds via aldehyde and aryl halide coupling, and the cross-coupling of arylthiophene derivatives through C-H functionalization. Moreover, it is applied in tandem nucleophilic allylation-alkoxyallylation reactions of alkynylaldehydes, enantioselective hydrosilylation of olefins, asymmetric allylic alkylation and amination, serving as a palladium source in cross-coupling reactions, often with Trost ligands, and in the carbostannylation of alkynes, and it acts as a precursor in the α-arylation of aldehydes.

December 01, 2024

Unparalleled Catalyst for Organic Synthesis

Using Alfa Chemistry's Allylpalladium(II) chloride dimer in our lab significantly enhanced our Heck and Suzuki-Miyaura reactions. This versatile catalyst streamlined our synthesis processes, proving indispensable for efficient cross-coupling reactions.