What is Palladium (II) Acetate?

Identification

Product Name:    Palladium (II) Acetate    

Synonyms:    ACETIC ACID PALLADIUM(II) SALT;PALLADIUM ACETATE;PALLADIUM(+2)ACETATE;PALLADIUM DIACETATE;PALLADIUM(II) ACETATE;PALLADIUM(II) ACETATE IN IONIC LIQUID ON SILICA;Pd(OAC)2 (=Palladium Acetate);PALLADIUM (II) ACETATE, TRIMER    

CAS:    3375-31-3    

MF:    C4H6O4Pd    

MW:    224.51    

EINECS:    222-164-4    

Properties

Melting point     205 °C    

Storage temp.     Store at R.T.    

Solubility     Soluble as monomer in glacial acetic acid or as trimer in benzene.    

Form     Various Forms In Red-(Powder/Flake/Crystalline/Beads)    

Color     Red-brown    

PH    2-3 (H2O, 20℃)(aqueous suspension)    

PH Range    2.0 - 3.0 at 20 °C    

Water Solubility     insoluble

Palladium(II) acetate is a chemical compound of palladium described by the formula [Pd(O2CCH3)2]n, abbreviated [Pd(OAc)2]n. It is more reactive than the analogous platinum compound. Depending on the value of n, the compound is soluble in many organic solvents and is commonly used as a catalyst for organic reactions.

Uses

Palladium (II) Acetate Trimer is used in Suzuki-Miyaura cross-coupling reactions. It also serves to catalyze the chemoselective reduction of nitroarenes.

Reactions

Efficient catalyst for the arylation of olefins (Heck reaction).

Catalyst for cross-coupling reactions.

Catalyst for C-H activation.

Precatalyst for enantioselective decarboxylative protonation of allyl β-ketoesters. 

Precursor to other Pd compounds

Palladium acetate is used to produce other palladium(II) compounds. For example, phenylpalladium acetate, used to isomerize allyl alcohols to aldehydes, is prepared by the following reaction:

Hg(C6H5)(OAc) + Pd(OAc)2 → Pd(C6H5)(OAc) + Hg(OAc)2

Palladium(II) acetate reacts with acetylacetone (the "acac" ligand) to produce Pd(acac)2.

Light or heat reduce palladium acetate to give thin layers of palladium and can produce nanowires and colloids.

Catalysis

Palladium acetate is a catalyst for many organic reactions, especially alkenes, dienes, and alkyl, aryl, and vinyl halides to form reactive adducts.

Reactions catalyzed by palladium(II) acetate:

Vinylation: An example is the Heck reaction and related processes.

Rearrangement of acyclic dienes: An example is the Cope rearrangement

Carbonylation reactions: for example, the formation of esters from aryl iodides, carbon monoxide, an alcohol or phenol.

Reductive amination of aldehydes or ketones by potassium formate.

Wacker process: the oxidation of ethylene by water to acetaldehyde (precursor to poly(vinyl acetate).

Buchwald-Hartwig amination of aryl halides/pseudohalides with alkyl an aryl amines.

conversion of aryl bromides into the trimethylsilanes, a functional group in many organic compounds including the fungicide "Latitude".

RC6H4Br + Si2(CH3)6 → RC6H4Si(CH3)3 + Si(CH3)3Br

Pd(O2CCH3)2 is compatible with the electronic properties of aryl bromides, and unlike other methods of synthesis, this method does not require high pressure equipment.

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