Skip to Content
Merck
All Photos(4)

Documents

669032

Sigma-Aldrich

PEPPSI™-IPr catalyst

98%, Umicore

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(4)

About This Item

Empirical Formula (Hill Notation):
C32H40Cl3N3Pd
CAS Number:
905459-27-0
Molecular Weight:
679.46
MDL number:
MFCD08457656
UNSPSC Code:
12352103
PubChem Substance ID:
24884825
NACRES:
NA.22

Quality Level

200

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

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)

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

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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.
View All Related Papers

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.

See All

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

Contact Technical Service