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697230

Sigma-Aldrich

[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)

Synonym(s):

Pd(dppf)Cl2

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About This Item

Linear Formula:
(C17H14P)2Fe · PdCl2
CAS Number:
72287-26-4
Molecular Weight:
731.70
EC Number:
460-040-3
MDL number:
MFCD00015757
UNSPSC Code:
12161600
PubChem Substance ID:
329761901
NACRES:
NA.22

form

powder

Quality Level

200

reaction suitability

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

mp

266-283 °C (lit.)

SMILES string

[Fe].Cl[Pd]Cl.[CH]1[CH][CH][C]([CH]1)P(c2ccccc2)c3ccccc3.[CH]4[CH][CH][C]([CH]4)P(c5ccccc5)c6ccccc6

InChI

1S/2C17H14P.2ClH.Fe.Pd/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;;;;/h2*1-14H;2*1H;;/q;;;;;+2/p-2

InChI key

JCWIWBWXCVGEAN-UHFFFAOYSA-L

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Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Catalyst for C-C and C-N coupling reaction.
Pd(dppf)Cl2 may be used as an effective palladium catalyst in the following reactions:
  • Cross-coupling of sec-alkyl and n-alkyl Grignard reagents with high yield and selectivity.
  • Suzuki coupling of aryl boronic esters with [11C]methyl iodide to form functionalized [11C]toluene derivatives.
  • Kumada cross-coupling of 1,3,5-tribromobenzene with Grignard reagents to form star-shaped oligothiophenes.
For small scale and high throughput uses, product is also available as ChemBeads (919780)

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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Electrophilic activation of benzaldehydes through ortho palladation: one-pot synthesis of 3-methylene-indan-1-ols through a domino allylstannylation/Heck reaction under neutral conditions.
Ján Cvengros et al.
Angewandte Chemie (International ed. in English), 48(33), 6148-6151 (2009-07-11)
Star?Shaped Oligothiophenes for Solution?Processible Organic Field?Effect Transistors.
Ponomarenko S
Advances in Functional Materials, 13(8), 591-596 (2003)
Shirbin, S. J. et al.
Tetrahedron Letters, 51, 2971-2971 (2010)
Dichloro [1,1?-bis (diphenylphosphino) ferrocene] palladium (II): an effective catalyst for cross-coupling reaction of a secondary alkyl grignard reagent with organic halides.
Hayashi T
Tetrahedron Letters, 20(21), 1871-1874 (1979)
Julien Monot et al.
Organic letters, 11(21), 4914-4917 (2009-10-06)
Complexes of triaryl- and trialkylboranes with N-heterocyclic carbenes (NHCs) participate in Suzuki-Miyaura cross-coupling reactions and provide coupled products in good yields under base-free conditions. The reaction can be applied to Csp(2)-Csp(2) and Csp(2)-Csp(3) carbon-carbon bond formation with triflates, iodides, bromides
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Articles

Syntheses of Functionalized Alkenes, Arenes, and Cycloalkenes via a Hydroboration-Coupling Sequence

Tandem hydroboration Suzuki Coupling both intermolecular and intramolecular gave diverse alkyl substituted products dppf

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