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924377

Sigma-Aldrich

Palladium(II) Acetate ChemBeads

Synonym(s):

Acetic acid palladium salt, Bis(acetato)palladium, Diacetatopalladium, Diacetoxypalladium

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About This Item

Linear Formula:
Pd(OCOCH3)2
CAS Number:
3375-31-3
MDL number:
MFCD00012453
UNSPSC Code:
12352302
NACRES:
NA.82

form

solid

Quality Level

100

composition

~ 4 wt.% loading of catalyst

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
core: palladium
reaction type: Heck Reaction
core: palladium
reaction type: Hiyama Coupling
core: palladium
reaction type: Negishi Coupling
core: palladium
reaction type: Sonogashira Coupling
core: palladium
reaction type: Stille Coupling
core: palladium
reaction type: Suzuki-Miyaura Coupling
reaction type: Cross Couplings
reagent type: catalyst

InChI

1S/2C2H4O2.Pd/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2

InChI key

YJVFFLUZDVXJQI-UHFFFAOYSA-L

Related Categories

General description

Palladium(II) acetate is a homogenous oxidation catalyst. It participates in the activation of alkenic and aromatic compounds towards oxidative inter- and intramolecular nucleophilic reactions. Crystals of palladium(II) acetate have a trimeric structure, having symmetry D3h. Each of the palladium atoms in the crystals are joined to the other two by double acetate bridges. Microencapsulation of palladium(II) acetate in polyurea affords polyurea-encapsulated palladium(II) acetate. It is a versatile heterogeneous catalyst for various phosphine-free cross-coupling reactions. It participates as catalyst in the Heck coupling reaction of pthalides with different alkenes.

Application

Catalyst for an intramolecular coupling of aryl bromides with alcohols giving 1,3-oxazepines. Preparation of cyclic ureas via palladium-catalyzed intramolecular cyclization.

ChemBeads are chemical coated glass beads. ChemBeads offer improved flowability and chemical uniformity perfect for automated solid dispensing and high-throughput experimentation. The method of creating ChemBeads uses no other chemicals or surfactants allowing the user to accurately dispense sub-milligram amounts of chemical.

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For larger scale uses, product also available in powdered form (205869) & (520764)

Other Notes

High-Throughput Reaction Screening with Nanomoles of Solid Reagents Coated on Glass Beads

Versatile Methods to Dispense Sub-Milligram Quantities of Solids using Chemical Coated Beads for High-Throughput Experimentation

ChemBead Enabled High-Throughput Cross-Electrophile Coupling Reveals a New Complementary Ligand

Signal Word

Danger

Hazard Statements

H317,H318,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Sens. 1A

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Novel formation of 1,3-oxazepine heterocycles via palladium-catalyzed intramolecular coupling reaction.
Ma Chen, et al.
Tetrahedron, 62, 9002-9009 (2006)
The First Stereoselective Palladium-Catalyzed Cyclocarbonylation of β,γ-Substituted Allylic Alcohols.
Brunner M, et al.
The Journal of Organic Chemistry, 62, 7565-7568 (1997)
Palladium-catalyzed β-arylation of modified vinyl ethers with aryl triflates..
Badone D, et al.
Tetrahedron Letters, 34, 3603-3606 (1993)
Palladium-Catalyzed Amination of Aryl Triflates.
Wolfe J P, et al.
The Journal of Organic Chemistry, 62, 1264-1267 (1997)
Mark McLaughlin et al.
Organic letters, 8(15), 3311-3314 (2006-07-14)
[Structure: see text] An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded
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