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Sigma-Aldrich

Allylpalladium(II) chloride dimer

greener alternative

98%

Synonym(s):

Bis((η3-allyl)(chloro)palladium), Di-ο-allyldi-μ-chlorodipalladium, [PdCl(C3H5)]2

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About This Item

Empirical Formula (Hill Notation):
C6H10Cl2Pd2
CAS Number:
12012-95-2
Molecular Weight:
365.89
Beilstein:
4124623
EC Number:
234-579-8
MDL number:
MFCD00044874
UNSPSC Code:
12161600
PubChem Substance ID:
24853328
NACRES:
NA.22

Quality Level

200

Assay

98%

form

solid

reaction suitability

core: palladium
reaction type: Cross Couplings
reagent type: catalyst
reaction type: C-H Activation

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

greener alternative category

, Aligned

storage temp.

2-8°C

SMILES string

Cl[Pd]CC=C.Cl[Pd]CC=C

InChI

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

InChI key

TWKVUTXHANJYGH-UHFFFAOYSA-L

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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.
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Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Allylpalladium(II) chloride dimer has been employed for the following studies:
  • Synthesis of cationic palladium cataysts, used in the microwave-assisted Heck arylation.
  • Synthesis of N-heterocyclic carbene-palladium-η3-allyl chloride complexes, which are efficient catalyst for the Suzuki-Miyaura cross-coupling of aryl bromides and activated aryl chlorides.
  • Synthesis of 1,4-diallyl-1,2-dihydroisoquinolines.
  • As catalyst for greener Buchwald-Hartwig coupling in TPGS-750-M.

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315

Hazard Classifications

Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Superhydrophobicity of nanostructured carbon films in a wide range of pH values.
Lin Feng et al.
Angewandte Chemie (International ed. in English), 42(35), 4217-4220 (2003-09-23)
Yasuyuki Harada et al.
Organic letters, 7(20), 4385-4387 (2005-09-24)
[reaction: see text] The reaction of yne esters with carbon monoxide (1 atm) in the presence of palladium complexes gives bicyclic unsaturated lactone derivatives in good to high yields. The 2-pyridinyloxy group is a good leaving group among leaving groups
An N-heterocyclic carbene-palladium-η3-allyl chloride complex for the Suzuki-Miyaura coupling of aryl halides.
Broekemier NW, et al.
European Journal of Chemistry, 5(1), 162-166 (2014)
Radetich, B.; RajanBabu, T. V.
Journal of the American Chemical Society, 120, 8007-8007 (1998)
Suzuki cross-couplings of alkyl tosylates that possess beta hydrogen atoms: synthetic and mechanistic studies.
Matthew R Netherton et al.
Angewandte Chemie (International ed. in English), 41(20), 3910-3912 (2002-10-19)
View All Related Papers

Articles

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

Protocols

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

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