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697230 Sigma-Aldrich

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

Synonym: Pd(dppf)Cl2

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Homogeneous Pd Catalysts, Palladium Catalysts
Quality Level   200
reaction suitability   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

Description

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.

Packaging

1, 5, 250 g in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Palladium-catalyzed inter- and intramolecular cross-coupling reactions of B-alkyl-9-borabicyclo[3.3.1]nonane derivatives with 1-halo-1-alkenes or haloarenes. Syntheses of functionalized alkenes, arenes, and cycloalkenes via a hydroboration-coupling sequence

The cross-coupling reaction of B-alkyl-9-borabicyclo[3.3.l]nonanes (B-R-9 BBN), readily obtainable from alkenes by hydroboration, with 1-halo-1-alkenes or haloarenes in the presence of a catalytic am...
Keywords: Catalysis, Chromatography, Column chromatography, Coupling reactions, Cross couplings, Oxidations

Related Content

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Palladium catalyzed cross-coupling reactions have revolutionized the way in which molecules are constructed. From the fields of organic synthesis and medicinal chemistry, to materials science and pol...
Keywords: Catalysis, Coupling reactions, Cross couplings, Materials Science, Medicinal chemistry, Organic synthesis, Polymer science, transformation

Peer-Reviewed Papers
15

References

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