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669032 Sigma-Aldrich

PEPPSI-IPr catalyst

98%

Synonym: [1,3-Bis(2,6-Diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Homogeneous Pd Catalysts, Palladium Catalysts
InChI Key   BLDKGTGQENJFON-UHFFFAOYSA-L
assay   98%
mp   230 °C

Description

Packaging

1 kg in poly bottle

250 g in poly bottle

1, 5 g in glass bottle

Application

• Catalyst for Kumada-Tamao-Corriu (KTC) reaction (eq. 1)
• Catalyst for Negishi coupling reaction (eq. 2)
• Catalyst for Suzuki coupling reaction (eq. 3)
• Catalyst for Buchwald-Hartwig amination reaction (eq. 4)
PEPPSI<SUP>™</SUP>-IPr catalyst

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Legal Information

PEPPSI is a trademark of Total Synthesis Ltd.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3

Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
Where can I find more information on the possible applications of Product 669032, PEPPSI-IPr catalyst?
ChemFiles 6.3 explores the advantages and reaction applications of the PEPPSI-IprTM catalyst.
When using Product 669032, PEPPSI-IPr catalyst, how can I remove any trace palladium from the reaction mixture after the reaction is complete?
You may be interested in the QuadraPure metal scavengers, like Product No. 665422. These functionalized beads can effectively remove selected trace metallic impurities in a relatively easy process.
What is the difference between Product 669032, PEPPSI-IPr catalyst, and the ChemDose version, Product 685143?
Both products are the same catalyst, but in different forms. Product 669032 is a powder, while 685143 is the catalyst in tablet form. A specific amount of catalyst (2μmol for 685143) is impregnated into an inert tablet matrix as a time-saving alternative to weighing out the catalyst. More information on the ChemDose tablets is found at:
How do I find price and availability?
There are several ways to find pricing and availability for our products.Once you log onto our website, you will find the price and availability displayed on the product detail page.You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 orview local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
My question is not addressed here, how can I contact Technical Service for assistance?
Ask a Scientist here.
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Protocols & Articles

Articles

Negishi cross-coupling of secondary alkylzinc halides with aryl/heteroaryl halides using Pd-PEPPSI-IPent

Over the past two decades, considerable attention has been given to the development of new ligands for the palladium-catalyzed arylation of amines and related NH-containing substrates (i.e. Buchwald-...
Keywords: Aminations, Arylations, Buchwald-Hartwig amination, Catalysis, Chromatography, Column chromatography, Cross couplings, Gas chromatography, Hydroaminations, Ligands, Thin layer chromatography

PEPPSI™ Catalyst - Introduction, advantages and applications

Professor Mike Organ, along with Drs. Chris O’Brien and Eric Kantchev, have developed an elegant Pd-NHC catalyst system. The title complex PEPPSI stands for Pyridine-Enhanced Precatalyst Preparation ...
William Sommer
Aldrich ChemFiles 2007, 7.10, 22.
Keywords: Aldrichimica Acta, Aminations, Buchwald-Hartwig amination, Chemfiles, Coupling reactions, Cross couplings, Eliminations, Fischer Indole Synthesis, Ligands, Protocols, Rearrangements, Reductive eliminations

PEPPSI™ Catalyst

Palladium has played a central role in the expeditious preparation of complex organic molecules, since the discovery and subsequent catalytic use of Pd(PPh3)4 by Malatesta, Angoletta and others.1 In ...
ChemFiles 2006, 6.3, 2.
Keywords: Addition reactions, Aminations, Arylations, Building blocks, Catalysis, Chromatography, Coupling reactions, Cross couplings, Eliminations, Fischer Indole Synthesis, Flash chromatography, Grignard Reaction, Heck Reaction, Hiyama Coupling, Ligands, Natural product synthesis, Negishi Coupling, Nuclear magnetic resonance spectroscopy, Oxidative additions, Rearrangements, Reductions, Reductive eliminations, Substitutions, Suzuki coupling, Suzuki reactions, Transmetalation

PEPPSI™ Catalysts

PEPPSI™-IPr: An air- and water-stable catalysts for industrially useful intermolecular cross-coupling reactions, aminations, and intramolecular Heck transformations.
Keywords: Addition reactions, Aminations, Arylations, Building blocks, Catalysis, Coupling reactions, Cross couplings, Eliminations, Fischer Indole Synthesis, Grignard Reaction, Ligands, Metathesis, Nuclear magnetic resonance spectroscopy, Oxidative additions, Rearrangements, Reductions, Reductive eliminations, Suzuki coupling, Suzuki reactions

PEPPSI™-IPent for Demanding Cross-Coupling Reactions

Professor Mike Organ and co-workers have developed the PEPPSI™ (Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation) precatalysts for palladium-catalyzed cross-coupling reactions. ...
Keywords: Aminations, Catalysis, Coupling reactions, Cross couplings, Ligands

PEPPSI™-IPr

Accelerate your small-molecule synthesis and drug discovery success with our innovative catalyst technologies. PEPPSI™-IPr is distinguished by higher efficiency and superior functional group toleranc...

Aldrich ChemFiles 2006, 6.6, 15.


Keywords: Arylations, Chemfiles, Drug discovery, Ligands

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

PEPPSI™ Catalysts in Chemical Synthesis

PEPPSI™-IPr: An air- and water-stable catalysts for industrially useful intermolecular cross-coupling reactions, aminations, and intramolecular Heck transformations.
Keywords: Addition reactions, Aminations, Arylations, Building blocks, Catalysis, Coupling reactions, Cross couplings, Eliminations, Fischer Indole Synthesis, Grignard Reaction, Ligands, Metathesis, Nuclear magnetic resonance spectroscopy, Oxidative additions, Rearrangements, Reductions, Reductive eliminations, Suzuki coupling, Suzuki reactions

Peer-Reviewed Papers
15

References

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