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697230

Sigma-Aldrich

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

Synonym(s):
Pd(dppf)Cl2
Linear Formula:
(C17H14P)2Fe · PdCl2
CAS Number:
Molecular Weight:
731.70
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

form

powder

reaction suitability

core: palladium
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

Application

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.

Packaging

1, 5, 250 g in glass bottle

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More Documents

Quotes and Ordering

Shirbin, S. J. et al.
Tetrahedron Letters, 51, 2971-2971 (2010)
Star?Shaped Oligothiophenes for Solution?Processible Organic Field?Effect Transistors.
Ponomarenko S
Advances in Functional Materials, 13(8), 591-596 (2003)
Palladium-catalyzed coupling of aldehyde-derived hydrazones: practical synthesis of triazolopyridines and related heterocycles.
Oliver R Thiel et al.
Angewandte Chemie (International ed. in English), 49(45), 8395-8398 (2010-07-28)
An improved synthesis of substituted [11C] toluenes via Suzuki coupling with [11C] methyl iodide
Hostetler E
Journal of Labelled Compounds & Radiopharmaceuticals, 48(9), 629-634 (2005)
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)

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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