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227994

Sigma-Aldrich

Bis(dibenzylideneacetone)palladium(0)

Synonyme(s) :

Palladium(0) bis(dibenzylideneacetone), Pd(dba)2

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Changer de vue
500 MG
51,80 €
2 G
132,00 €
5 G
197,00 €
50 G
1 630,00 €

About This Item

Formule linéaire :
(C6H5CH=CHCOCH=CHC6H5)2Pd
Numéro CAS:
32005-36-0
Poids moléculaire :
575.00
Numéro MDL:
MFCD00051942
Code UNSPSC :
12161600
ID de substance PubChem :
24853668
Nomenclature NACRES :
NA.22

51,80 €

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Forme

powder

Niveau de qualité

100

Pertinence de la réaction

core: palladium
reagent type: catalyst

Capacité de réaction

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling

Chaîne SMILES 

[Pd].O=C(/C=C/c1ccccc1)\C=C\c2ccccc2.O=C(/C=C/c3ccccc3)\C=C\c4ccccc4

InChI

1S/2C17H14O.Pd/c2*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;/h2*1-14H;/b2*13-11+,14-12+;

Clé InChI

UKSZBOKPHAQOMP-SVLSSHOZSA-N

Description générale

Bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) is an air stable Pd0 complex. It is a reagent for the synthesis of allylic substituted cyclopentadienes.[1] It is a homogeneous catalyst.[2][3] It catalyzes the alkylation of allyl acetates by various nucleophiles under mild conditions.[4]

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) was employed as catalyst in the following studies:
  • Synthesis of isomeric 2-aryl-2,5-dihydrofurans, via Heck coupling of aryl bromides with alkenes using neopentyl phosphine ligands.[5]
  • Heck reaction of benzyl trifluoroacetate and 2,3-dihydrofuran phosphoramidite ligand.[6]
  • Allylation of stabilized anions.[7]
  • Cross coupling of allyl, alkenyl and aryl halides with organostannanes.[7]
  • Cross coupling of vinyl halides with alkenyl zinc species.[7]
  • Carbonylation of alkenyl and aryl halides.[7]
  • Employed with cyclic thiourea ligands in an efficient aerobic oxidation of alcohols to aldehydes and ketones.[8]

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
MKCW4974
MKCW0564
MKCV6896
MKCT9164
MKCV3293

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Cuerva, J. M.; Gomez-Bengoa, E.; et al
The Journal of Organic Chemistry, 62, 7540-7540 (1997)
Tetrahedron Letters, 22, 1399-1399 (1981)
Xiaoxiang Liu et al.
Journal of the American Chemical Society, 126(16), 5182-5191 (2004-04-22)
A general procedure for the palladium-catalyzed arylation of trimethylsilyl enolates of esters and imides is reported. In the presence of ZnF2 or Zn(O-t-Bu)2 as an additive, the trimethylsilyl enolates of esters, including those bearing alpha-alkoxy derivatives, underwent arylation in high
T Vats et al.
Scientific reports, 6, 33053-33053 (2016-09-14)
Amazing conductivity, perfect honeycomb sp(2) arrangement and the high theoretical surface area make pristine graphene as one of the best materials suited for application as catalyst supports. Unfortunately, the low reactivity of the material makes the formation of nanocomposite with
Macsari, I.; Hupe, E.; Szabo, K. J.
The Journal of Organic Chemistry, 64, 9547-9547 (1999)
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  1. How can I determine the shelf life / expiration / retest date of this product?

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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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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    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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