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Sigma-Aldrich

PEPPSI™-SIPr catalyst

Umicore

Sinonimo/i:

(1,3-Bis(2,6-diisopropylphenyl)imidazolidene) ( 3-chloropyridyl) palladium(II) dichloride

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About This Item

Formula empirica (notazione di Hill):
C32H42Cl3N3Pd
Numero CAS:
927706-57-8
Peso molecolare:
681.47
Codice UNSPSC:
12161600
ID PubChem:
24885231
NACRES:
NA.22

Impiego in reazioni chimiche

core: palladium
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

Produttore/marchio commerciale

Umicore

Punto di fusione

229-230 °C

Stringa SMILE

Cl[Pd]Cl.Clc1cccnc1.CC(C)c2cccc(C(C)C)c2N3[CH]N(CC3)c4c(cccc4C(C)C)C(C)C

InChI

1S/C27H39N2.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;;;/h9-14,17-21H,15-16H2,1-8H3;1-4H;2*1H;/q;;;;+2/p-2
BWASJRFNPJXAGT-UHFFFAOYSA-L

Applicazioni

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Catalyst for C-C and C-N coupling reactions.

Note legali

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.

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302 + H312 + H332

Classi di pericolo

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
MKCM0118
MKCL1541
MKBW1286V
MKBN6693V
MKBJ8346V

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Organ, Michael G.; Abdel-Hadi, Mirvat; et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 12, 150-150 (2006)
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
Michael G Organ et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(8), 2443-2452 (2008-01-29)
Pd-N-heterocyclic carbene (NHC)-catalyzed Buchwald-Hartwig amination protocols mediated by Pd-PEPPSI precatalysts is described. These protocols provide access to a range of hindered and functionalized drug-like aryl amines in high yield with both electron-deficient and electron-rich aryl- and heteroaryl chlorides and bromides.

Articoli

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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