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701602

Sigma-Aldrich

1,1′-Bis-(di-tert.-butylphosphino-)ferrocen-palladiumdichlorid

greener alternative

98%

Synonyme(s) :

PdCl2(dtbpf)

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About This Item

Formule empirique (notation de Hill):
C26H44Cl2FeP2Pd
Numéro CAS:
Poids moléculaire :
651.75
Numéro MDL:
Code UNSPSC :
12161600
ID de substance PubChem :
Nomenclature NACRES :
NA.22

Pureté

98%

Forme

powder

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

Caractéristiques du produit alternatif plus écologique

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

Pf

203-208 °C

Autre catégorie plus écologique

Température de stockage

−20°C

Chaîne SMILES 

[Fe].Cl[Pd]Cl.CC(C)(C)P([C]1[CH][CH][CH][CH]1)C(C)(C)C.CC(C)(C)P([C]2[CH][CH][CH][CH]2)C(C)(C)C

InChI

1S/2C13H22P.2ClH.Fe.Pd/c2*1-12(2,3)14(13(4,5)6)11-9-7-8-10-11;;;;/h2*7-10H,1-6H3;2*1H;;/q;;;;;+2/p-2

Clé InChI

JQZFOBWXNREQLO-UHFFFAOYSA-L

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Description générale

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.
[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dtbpf)) participates as catalyst in Suzuki and Heck reactions. It is a preformed catalyst synthesized by a group of researchers at Johnson Matthey′s Catalysis and Chiral Technologies. It is an active catalyst for various Pd catalyzed cross-coupling reactions.
[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) is an air-stable, highly active and versatile catalyst. It is an efficient catalyst for cross-coupling reactions. It participates as catalyst in various coupling reactions of the fine chemicals and pharmaceutical chemicals. It is commonly employed as homogeneous catalyst in the Suzuki reactions.

PdCl2(dtbpf) is an air-stable cross-coupling catalyst used in the Suzuki coupling of various aryl chlorides.

Application

[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dtbpf)) may be used as catalyst in the Suzuki cross-coupling reaction of various aromatic and heteroaromatic halides with methyliminodiacetic acid derivatives (MIDA boronates) at room temperature (in the absence of organic solvent). It may be employed as catalyst for the synthesis of chalcones, via cross-coupling reactions.
[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) was used in the preparation of [PdCl2(bisphosphinometallocene)] complexes. These complexes are reported to be the catalyst precursors for the Buchwald-Hartwig reaction.
It is also employed as catalyst for greener Suzuki cross-coupling in TPGS-750-M.

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

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)


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Bruce H Lipshutz et al.
Organic letters, 10(7), 1329-1332 (2008-03-14)
A nonionic amphiphile such as Triton X-100 or the vitamin E-based PTS, both of which form nanomicelles in water, promotes Heck cross-couplings of non-water-soluble partners at ambient temperatures. These are the first examples of Heck reactions conducted in water (as
Gabriela A Grasa et al.
Organic letters, 9(26), 5489-5492 (2007-11-23)
alpha-Arylation of various ketones with aryl chlorides and bromides using the well-defined and air-stable (DtBPF)PdX2 (X = Cl, Br) catalysts gave 80-100% yield of the coupled products under relatively mild conditions at low catalyst loadings. The X-ray structure of (DtBPF)PdCl2
The 2010 Nobel Prize in chemistry: palladium-catalysed cross-coupling.
Colacot TJ.
Platinum Metals Rev., 55(2), 84-90 (2011)
Natural and Synthetic Chalcones: Tools for the Study of Targets of Action-Insulin Secretagogue or Insulin Mimetic?
Nunes RJ, et al.
Stud. Nat. Prod. Chem., 39, 62-62 (2013)
Synthesis and electrochemistry of late transition metal complexes containing 1, 1'-bis (dicyclohexylphosphino) ferrocene (dcpf). The X-ray structure of [PdCl 2 (dcpf)] and Buchwald-Hartwig catalysis using [PdCl2(bisphosphinometallocene)] precursors.
Hagopian LE, et al.
Journal of Organometallic Chemistry, 691(23), 4890-4900 (2006)

Articles

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.

Protocoles

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

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