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222380

Sigma-Aldrich

Allylpalladium(II) chloride dimer

greener alternative

98%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C6H10Cl2Pd2
Número de CAS:
12012-95-2
Peso molecular:
365.89
Beilstein/REAXYS Number:
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

signalword

Warning

hcodes

H315

Hazard Classifications

Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificados de análisis (COA)

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Efficient Heck vinylation of aryl halides catalyzed by a new air-stable palladium-tetraphosphine complex.
M Feuerstein et al.
The Journal of organic chemistry, 66(17), 5923-5925 (2001-08-21)
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)
Tandem nucleophilic allylation-alkoxyallylation of alkynylaldehydes via amphiphilic bis-p-allylpalladium complexes.
Nakamura H, et al.
Tetrahedron Letters, 43(42), 7631-7633 (2002)
Radetich, B.; RajanBabu, T. V.
Journal of the American Chemical Society, 120, 8007-8007 (1998)
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)
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Artículos

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.

Protocolos

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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