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Merck
CN

669032

PEPPSI-IPr catalyst

98%, Umicore

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C32H40Cl3N3Pd
CAS Number:
Molecular Weight:
679.46
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
MDL number:
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Product Name

PEPPSI-IPr catalyst, 98%, Umicore

Quality Level

assay

98%

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

230 °C

SMILES string

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

InChI key

BLDKGTGQENJFON-UHFFFAOYSA-L

General description

PEPPSI-IPr catalyst widely used in carbonylative cross-coupling reactions.

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

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

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

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves



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Articles

Choose Ascentis® Express Peptide ES-C18 U/HPLC Columns based on Fused-Core® technology for fast and efficient separation of high-molecular weight compounds, such as peptides and small proteins. With a 2.7 µm particle size and rigorous testing, these columns offer reliable results and high efficiency.

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

Professor Mike Organ and co-workers have developed the PEPPSI™ (Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation) precatalysts for palladium-catalyzed cross-coupling reactions.


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)
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



Global Trade Item Number

SKUGTIN
669032-1KG04061826680360
669032-1G04061832734910
669032-5G04061832734927
669032-250G04061833399514