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339768

Sigma-Aldrich

Tetrakis(acetonitrile)palladium(II) tetrafluoroborate

Synonym(s):

NSC 307191, Palladium(II) tetrafluoroborate tetraacetonitrile complex

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About This Item

Linear Formula:
Pd(CH3CN)4(BF4)2
CAS Number:
21797-13-7
Molecular Weight:
444.24
MDL number:
MFCD00043297
UNSPSC Code:
12161600
PubChem Substance ID:
24860675
NACRES:
NA.22

form

solid

reaction suitability

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
core: palladium
reagent type: ligand

mp

230 °C (dec.) (lit.)

SMILES string

[Pd++].CC#N.CC#N.CC#N.CC#N.F[B-](F)(F)F.F[B-](F)(F)F

InChI

1S/4C2H3N.2BF4.Pd/c4*1-2-3;2*2-1(3,4)5;/h4*1H3;;;/q;;;;2*-1;+2

InChI key

YWMRPVUMBTVUEX-UHFFFAOYSA-N

General description

Tetrakis(acetonitrile)palladium(II) tetrafluoroborate is a stronger Lewis acid. It participates in the preparation of 2:1 complex [Pd(1,2-bis(2′-pyridylethynyl)benzene)2](BF4]2, by Sonogashira cross-coupling reaction.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Reactant involved in:
  • Reactions where it plays a role as the metal source due to weakly coordinated acetonitrile ligands

Precursor for:
  • Synthesis of dendritic SCS-pincer palladium complexes
  • Palladium complexes of click ligands
  • Dipalladium catalysts for use in Heck cross-coupling, Suzuki cross-coupling, and aldehyde olefination

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H332

Precautionary Statements

P261 - P271 - P304 + P340 + P312

Hazard Classifications

Acute Tox. 4 Inhalation

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)

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Takashi Nishikata et al.
Journal of the American Chemical Society, 132(14), 4978-4979 (2010-03-24)
Cationic palladium(II) catalyst realized facile C-H activation of aryl urea with arylboronic acids at room temperature. This reaction is extremely mild to carry out aromatic C-H activations through electrophilic substitution.
Maud Reiter et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(27), 7190-7203 (2006-07-05)
Structurally diverse beta-hydroxyenones are shown to undergo nonoxidative 6-endo-trig ring closure to form highly substituted tetrahydropyranones. Amberlyst-15, Al(ClO(4))(3) x 9 H(2)O and [Pd(MeCN)(4)](BF(4))(2) were found to be suitable catalysts for these intramolecular conjugate additions, preventing side reactions, such as dehydration
Yun Fu Chan et al.
Dalton transactions (Cambridge, England : 2003), (32)(32), 3538-3545 (2007-08-08)
Extended-chain complexes containing multiple transition metal centres linked by conjugated micro-cyanodiazenido(1-) ligands [N=N-C[triple bond, length as m-dash]N]- have been obtained by reaction of trans-[BrW(dppe)2(N2CN)], , [dppe=1,2-bis(diphenylphosphino)ethane] with dirhodium(II) tetra-acetate, bis(benzonitrile)palladium(II) dichloride, and bis(aqua)M(II) bis(hexafluoroacetylacetonate) (M=Mn, Ni, Cu, Zn): stronger Lewis
Adam M Johns et al.
Journal of the American Chemical Society, 128(6), 1828-1839 (2006-02-09)
We report a catalyst for intermolecular hydroamination of vinylarenes that is substantially more active for this process than catalysts published previously. With this more reactive catalyst, we demonstrate that additions of amines to vinylarenes and dienes occur in the presence
Gorman, C. B.; Vest, R. W. et al.
Macromolecules, 32, 4157-4157 (1999)
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Articles

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.

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