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674702

Sigma-Aldrich

PEPPSI™-SIPr catalyst

Umicore

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C32H42Cl3N3Pd
CAS Number:
927706-57-8
Molecular Weight:
681.47
UNSPSC Code:
12161600
PubChem Substance ID:
24885231
NACRES:
NA.22

reaction suitability

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

manufacturer/tradename

Umicore

mp

229-230 °C

SMILES string

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

InChI key

BWASJRFNPJXAGT-UHFFFAOYSA-L

Application

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

Legal Information

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.

pictograms

Exclamation mark
GHS07

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Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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.

Articles

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 Stabilization and Initiation.

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

PEPPSI™ Catalysts are novel state-of-the-art catalyst that successfully performs cross-coupling niche reactions.

PEPPSI™ Catalysts

Explore the higher efficiency and superior functional group tolerance of the Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation (PEPPSI™) palladium N-heterocyclic-carbene catalyst system.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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