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732117

Sigma-Aldrich

Pd-PEPPSI™-IPent catalyst

≥95%

Synonym(s):

Dichloro[1,3-bis(2,6-Di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II), [1,3-Bis(2,6-Di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)dichloropalladium(II), [1,3-Bis(2,6-Di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride

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About This Item

Empirical Formula (Hill Notation):
C40H56Cl3N3Pd
CAS Number:
1158652-41-5
Molecular Weight:
791.67
UNSPSC Code:
12161600
PubChem Substance ID:
329764705
NACRES:
NA.22

Quality Level

200

Assay

≥95%

form

solid

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

mp

195-201 °C

storage temp.

−20°C

SMILES string

Clc1cccnc1.CCC(CC)c2cccc(C(CC)CC)c2N3C=CN(c4c(cccc4C(CC)CC)C(CC)CC)\C3=[Pd](/Cl)Cl

InChI

1S/C35H52N2.C5H4ClN.2ClH.Pd/c1-9-26(10-2)30-19-17-20-31(27(11-3)12-4)34(30)36-23-24-37(25-36)35-32(28(13-5)14-6)21-18-22-33(35)29(15-7)16-8;6-5-2-1-3-7-4-5;;;/h17-24,26-29H,9-16H2,1-8H3;1-4H;2*1H;/q;;;;+2/p-2

InChI key

BCXSKTXOKALLAZ-UHFFFAOYSA-L

Related Categories

General description

Pd-PEPPSI™-IPent catalyst is a palladium-based catalyst used in cross-coupling reactions to form C-N and C- C bonds.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Cross-Coupling, Amination and Heck Transformation using PEPPSI Catalysts
  • Catalyst for Stille coupling reaction (eq. 1)
  • Catalyst for Negishi coupling reaction (eq. 2)
  • Catalyst for Suzuki coupling reaction (eq. 3)
Reaction scheme for Pd catalyst PEPPSI<SUP>™</SUP>-IPent used in cross coupling reaction
For small scale and high throughput uses, product is also available as ChemBeads (928399)

Legal Information

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

732117-1G:
732117-5G:
732117-BULK:
732117-250MG:
732117-VAR:
732117-50G:

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’.

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Pd-PEPPSI-IPent: low-temperature negishi cross-coupling for the preparation of highly functionalized, tetra-ortho-substituted biaryls.
Selçuk Calimsiz et al.
Angewandte Chemie (International ed. in English), 49(11), 2014-2017 (2010-02-18)
Pd-PEPPSI-IPentCl: A Useful Catalyst for the Coupling of 2-Aminopyridine Derivatives
Khadra A, et al.
Chemistry?A European Journal , 23(13), 3206-3212 (2017)
Meenakshi Dowlut et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(14), 4279-4283 (2010-03-09)
The reactivity of Pd-PEPPSI (Pyridine, Enhanced, Precatalyst, Preparation, Stabilization, and Initiation) precatalysts in the Stille-Migita cross-coupling reaction between heteroaryl stannanes and aryl or heteroaryl halides was evaluated. In general, Pd-PEPPSI-IPent (IPent=diisopentylphenylimidazolium derivative) demonstrated high efficiency over a variety of challenging
Michael G Organ et al.
Angewandte Chemie (International ed. in English), 48(13), 2383-2387 (2009-02-20)
Incredible Bulk: A series of N-heterocyclic carbene catalysts (see picture) were prepared and evaluated in the Suzuki-Miyaura reaction. A variety of sterically encumbered tetra-ortho-substituted biaryl products were formed from unreactive aryl chlorides using the isopentyl-substituted catalyst at temperatures ranging from
Pd-PEPPSI-IPent: An Active, Sterically Demanding Cross-Coupling Catalyst and Its Application in the Synthesis of Tetra-Ortho-Substituted Biaryls
Organ MG, et al.
Angewandte Chemie (International Edition in English), 48(13), 2383-2387 (2009)
View All Related Papers

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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.

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KitAlysis™ Suzuki-Miyaura Cross-Coupling Kit

Tools aid in kit setup for organic chemistry techniques, ensuring ease and success.

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