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669032

Sigma-Aldrich

PEPPSI™-IPr catalyst

98%, Umicore

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C32H40Cl3N3Pd
Numéro CAS:
905459-27-0
Poids moléculaire :
679.46
Numéro MDL:
MFCD08457656
Code UNSPSC :
12352103
ID de substance PubChem :
24884825
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Niveau de qualité

200

Essai

98%

Pertinence de la réaction

core: palladium
reagent type: catalyst

Capacité de réaction

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

Fabricant/nom de marque

Umicore

Pf

230 °C

Chaîne SMILES 

Cl[Pd]Cl.Clc1cccnc1.CC(C)c2cccc(C(C)C)c2N3CN(C=C3)c4c(cccc4C(C)C)C(C)C

InChI

1S/C27H38N2.C5H4ClN.2ClH.Pd/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;6-5-2-1-3-7-4-5;;;/h9-16,18-21H,17H2,1-8H3;1-4H;2*1H;/q;;;;+2/p-2

Clé InChI

BLDKGTGQENJFON-UHFFFAOYSA-L

Description générale

PEPPSI™-IPr catalyst widely used in carbonylative cross-coupling reactions.[1]

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
  • Catalyst for Kumada-Tamao-Corriu (KTC) reaction[2] (eq. 1)
  • Catalyst for Negishi coupling reaction[3] (eq. 2)
  • Catalyst for Suzuki coupling reaction[4] (eq. 3)
  • Catalyst for Buchwald-Hartwig amination reaction[5] (eq. 4)
PEPPSI<SUP>™</SUP>-IPr catalyst

For small scale and high throughput uses, product is also available as ChemBeads (931063)

Informations légales

Product of Umicore

This product, its manufacturing or use, is the subject of one or more issued or pending U.S. Patents (and foreign equivalents) owned or controlled by Umicore PMC. The purchase of this product from Umicore PMC through Sigma-Aldrich, its affiliates or their authorized distributors conveys to the buyer a limited, one-time, non-exclusive, non-transferable, non-assignable license. Buyer′s use of this product may infringe patents owned or controlled by third parties. It is the sole responsibility of buyer to ensure that its use of the product does not infringe the patent rights of third parties or exceed the scope of the license granted herein.

For any further information on product please refer to your local Umicore PMC contact at http://www.pmc.umicore.com

Patented, U.S. Pat. No. 7,250,510. Sold under an exclusive license from Total Synthesis Ltd.
PEPPSI is a trademark of Total Synthesis Ltd.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302 + H312 + H332

Classification des risques

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Faites votre choix parmi les versions les plus récentes :

Certificats d'analyse (COA)

Lot/Batch Number
MKCR1044
MKBX5997V
STBG1185V
STBG1186V
STBG0020V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Organ, M. G.; Abdel-Hadi, M. et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 150, 150-150 (2007)
Facile access to sterically hindered aryl ketones via carbonylative cross-coupling: application to the total synthesis of luteolin
O?Keefe BM, et al.
Tetrahedron, 67(24), 4344-4351 (2011)
Michael G Organ et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 13(1), 150-157 (2006-12-05)
An easily employed, highly versatile Kumada-Tamao-Corriu (KTC) protocol utilizing the PEPPSI (Pyridine, Enhanced, Precatalyst, Preparation, Stabilization and Initiation) precatalysts 1 and 2 is detailed. The ease-of-use of these catalysts and the synthesis of a wide range of hindered biaryls, large
Jørn Eivind Tungen et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 20(45), 14575-14578 (2014-09-17)
The first total synthesis of the lipid mediator MaR1n-3 DPA (5) has been achieved in 12 % overall yield over 11 steps. The stereoselective preparation of 5 was based on a Pd-catalyzed sp(3) -sp(3) Negishi cross-coupling reaction and a stereocontrolled Evans-Nagao acetate
Michael G Organ et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(18), 4749-4755 (2006-03-29)
We have developed the first user-friendly Negishi protocol capable of routinely cross-coupling all combinations of alkyl and aryl centers. The use of an easily synthesized, air stable, highly active, well-defined precatalyst PEPPSI-IPr (1; PEPPSI=pyridine-enhanced precatalyst preparation, stabilization and initiation; IPr=diisopropylphenylimidazolium
Afficher tous les articles scientifiques apparentés

Articles

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.

PEPPSI™ Catalysts Overview

PEPPSI™ palladium N-heterocyclic-carbene catalyst system enhances efficiency and functional group tolerance in catalysis.

PEPPSI™ Catalysts Overview

PEPPSI™ palladium N-heterocyclic-carbene catalyst system enhances efficiency and functional group tolerance in catalysis.

PEPPSI™ Catalysts Overview

PEPPSI™ palladium N-heterocyclic-carbene catalyst system enhances efficiency and functional group tolerance in catalysis.

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Questions

1–6 of 6 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. What is the Department of Transportation shipping information for this product?

    1 answer

    1. 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.

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  4. Where can I find more information on the possible applications of Product 669032, PEPPSI™-IPr catalyst?

    1 answer

    1. ChemFiles 6.3 explores the advantages and reaction applications of the PEPPSI-IprTM catalyst.

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  5. When using Product 669032, PEPPSI™-IPr catalyst, how can I remove any trace palladium from the reaction mixture after the reaction is complete?

    1 answer

    1. 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.

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  6. What is the difference between Product 669032, PEPPSI™-IPr catalyst, and the ChemDose version, Product 685143?

    1 answer

    1. 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:

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