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701998

Sigma-Aldrich

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

98%

Synonym(s):

PdCl2(dcypf)

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About This Item

Empirical Formula (Hill Notation):
C34H52Cl2FeP2Pd
CAS Number:
917511-90-1
Molecular Weight:
755.90
MDL number:
MFCD11656081
UNSPSC Code:
12161600
PubChem Substance ID:
329762337
NACRES:
NA.22

Assay

98%

form

powder

reaction suitability

core: palladium
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
reagent type: catalyst

mp

294-300 °C

storage temp.

−20°C

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/2C17H26P.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*7-8,13-16H,1-6,9-12H2;2*1H;;/q;;;;;+2/p-2

InChI key

HRAMBTUEZQOQRK-UHFFFAOYSA-L

Application

1,1′-Bis(di-cyclohexylphosphino)ferrocene]dichloropalladium(II) or (Pd(dcpf)Cl2) can be used as a catalyst in the synthesis of:
  • α, β-unsaturated amides by hydroaminocarbonylation of alkynes with tertiary amines.
  • Quinazoline derivatives via Suzuki-Miyaura coupling reaction between of quinazolines containing unprotected NH2 group and arylboronic acids.
  • α-aryl carbonyl compounds by α-arylation of ketones with aryl chlorides and aryl bromides.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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A highly practical and general route for α-arylations of ketones using Bis-phosphinoferrocene-based palladium catalysts
Grasa GA and Colacot TJ
Organic Process Research & Development, 12(3), 522-529 (2008)
Palladium-catalyzed hydroaminocarbonylation of alkynes with tertiary amines via C-N bond cleavage
Gao, Bao and Huang, Hanmin
Organic Letters, 19(22), 6260-6263 (2017)
Suzuki-Miyaura coupling of quinazolines containing an unprotected NH2 group: Synthesis and biological testing of quinazoline derivatives
Pulipati Y, et al.
Synthetic Communications, 47(12), 1142-1150 (2017)

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