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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

Quality Level

100

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW0392
MKCM0118
MKCL1541
MKBW1286V
MKBN6693V

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Organ, Michael G.; Abdel-Hadi, Mirvat; et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 12, 150-150 (2006)
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.
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

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.

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