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Allylpalladium(II) chloride dimer

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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:
4124623
Número CE:
234-579-8
Número MDL:
MFCD00044874
Código UNSPSC:
12161600
ID de la sustancia en PubChem:
24853328
NACRES:
NA.22
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Nivel de calidad

200

Ensayo

98%

Formulario

solid

idoneidad de la reacción

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

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Catalysis
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categoría alternativa más sostenible

, Aligned

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

TWKVUTXHANJYGH-UHFFFAOYSA-L

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Descripción general

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.[1]
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Aplicación

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.[2]
  • 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.[3]
  • Synthesis of 1,4-diallyl-1,2-dihydroisoquinolines.[4]
  • 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

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H315

Clasificaciones de peligro

Skin Irrit. 2

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
0000335391
0000335391
0000287837
MKCS9452
0000287837

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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)
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)
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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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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