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Sigma-Aldrich

Bis(triphenylphosphine)palladium(II) dichloride

98%

Sinonimo/i:

Dichlorobis(triphenylphosphine)palladium(II), Palladium(II)bis(triphenylphosphine) dichloride, PdCl2(PPh3)2

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About This Item

Formula condensata:
[(C6H5)3P]2PdCl2
Numero CAS:
Peso molecolare:
701.90
Beilstein:
4935975
Numero CE:
Numero MDL:
Codice UNSPSC:
12161600
ID PubChem:
NACRES:
NA.22

Livello qualitativo

Saggio

98%

Forma fisica

solid

Impiego in reazioni chimiche

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
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
reagent type: catalyst

Stringa SMILE

Cl[Pd]Cl.c1(P(c2ccccc2)c3ccccc3)ccccc1.c4(P(c5ccccc5)c6ccccc6)ccccc4

InChI

1S/2C18H15P.2ClH.Pd/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;/h2*1-15H;2*1H;/q;;;;+2/p-2
YNHIGQDRGKUECZ-UHFFFAOYSA-L

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Descrizione generale

Bis(triphenylphosphine)palladium(II) dichloride ((PdCl2(PPh3)2) is an organopalladium complex containing tertiary phosphine ligands that is commonly used in C-C bond forming reactions such as Heck arylation, Suzuki coupling, Stille coupling, and Sonogashira coupling.

Applicazioni

Bis(triphenylphosphine)palladium(II) dichloride can be used as a catalyst in the:
  • Coupling of 2-iodoanisole and terminal alkynes to synthesize 2,3-disubstituted benzofurans.
  • Copper-free Sonogashira cross-coupling reaction to synthesize diphenylacetylene.
  • Regioselective hydrocarboxylation of styrene.
  • Negishi coupling of fluoroarylzinc pivalates to prepare fluorinated oligophenyls.
  • Coupling of iodo-α-β-unsaturated esters to afford tetrasubstituted olefins.
For small scale and high throughput uses, product is also available as ChemBeads (927759)

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Descrizione
Determinazione del prezzo

Pittogrammi

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Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

Aquatic Chronic 4 - Skin Sens. 1A

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


Certificati d'analisi (COA)

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Phenoxide-assisted P-C bond cleavage in PdCl2 (PPh3) 2 under very mild conditions
Yasuda H, et al.
Journal of Organometallic Chemistry, 691, 1307-1310 (2006)
Alison B Lemay et al.
The Journal of organic chemistry, 71(9), 3615-3618 (2006-04-22)
The efficient regioselective and stereospecific synthesis of tetrasubstituted olefins using a mild and convenient method is disclosed. 2-Alkynyl esters are selectively converted to E-beta-chloro-alpha-iodo-alpha,beta-unsaturated esters by exposure to Bu4NI in refluxing dichloroethane. These products are produced cleanly, regio- and stereoselectively
Synthesizing Highly Fluorinated Oligophenyls via Negishi Coupling of Fluoroarylzinc Pivalates
Engelage E
Synthesis, 54, 711-722 (2021)
PdCl2 (PPh3)2-heteropolyacids-catalyzed regioselective hydrocarboxylation of styrene
J. Mol. Catal. A: Chem., 182, 195-207 (2002)
Modular Synthesis of Phosphino Hydrazones and Their Use as Ligands in a Palladium-Catalysed Cu-Free Sonogashira Cross-Coupling Reaction
Baweja S, et al.
ChemPlusChem, e202300163-e202300163 (2023)

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