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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

Niveau de qualité

200

Pureté

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.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
  • 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

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
MKBX5997V
STBG1185V
STBG1186V
STBG0020V
STBF9237V

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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
Organ, M. G.; Abdel-Hadi, M. et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 150, 150-150 (2007)
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
Eric Assen B Kantchev et al.
Angewandte Chemie (International ed. in English), 46(16), 2768-2813 (2007-04-06)
Palladium-catalyzed C-C and C-N bond-forming reactions are among the most versatile and powerful synthetic methods. For the last 15 years, N-heterocyclic carbenes (NHCs) have enjoyed increasing popularity as ligands in Pd-mediated cross-coupling and related transformations because of their superior performance
Afficher tous les articles scientifiques apparentés

Articles

PEPPSI™ Catalyst - Introduction, advantages and applications

PEPPSI™ Catalyst - Introduction, advantages and applications

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

Professor Mike Organ at York University, along with co-workers Dr. Chris O’Brien and Dr. Eric Kantchev, have developed an palladium N-heterocyclic-carbene (NHC) catalyst system. They reacted PdCl2with a bulky NHC ligand, 2,6-diisopropylphenyllimidazolium chloride (IPr), and an α-donating 3-chloropyridine ligand for stability. The title complex, PEPPSI™, stands for Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation. Sigma-Aldrich offesr gram-scale quantities of the PEPPSI™ catalyst in collaboration with the Organ research group.

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