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Sigma-Aldrich

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

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Synonym(s):
Pd(dppf)Cl2
Linear Formula:
(C17H14P)2Fe · PdCl2
CAS Number:
72287-26-4
Molecular Weight:
731.70
EC Number:
460-040-3
MDL number:
MFCD00015757
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

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Palladium-catalysed cyclisation of N-alkynyl aminomalonates.
Wilfried Hess et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(41), 12303-12306 (2010-09-15)
Shunsuke Chiba et al.
Journal of the American Chemical Society, 131(36), 12886-12887 (2009-08-25)
A Pd(II)-catalyzed ring expansion-reaction of cyclic 2-azidoalcohol derivatives was found to proceed via an unprecedented C-C bond cleavage-C-N bond formation sequence, providing substituted azaheterocycles.
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)
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)
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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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