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Merck

732117

Pd-PEPPSI™-IPent catalyst

≥95%, solid

Sinónimos:

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

Fórmula empírica (notación de Hill):
C40H56Cl3N3Pd
Número CAS:
1158652-41-5
Peso molecular:
791.67
MDL number:
MFCD34166665
UNSPSC Code:
12161600
PubChem Substance ID:
329764705
NACRES:
NA.22

Nombre del producto

Pd-PEPPSI™-IPent catalyst, ≥95%

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

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

Quality Level

200

Categorías relacionadas

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.

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)

General description

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
MKCZ9376
MKDB0435
MKCZ3891
MKCZ1942
MKCX9590

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Visite la Librería de documentos

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)
Cory Valente et al.
Angewandte Chemie (International ed. in English), 51(14), 3314-3332 (2012-01-31)
Palladium-catalyzed cross-coupling reactions enable organic chemists to form C-C bonds in targeted positions and under mild conditions. Although phosphine ligands have been intensively researched, in the search for even better cross-coupling catalysts attention has recently turned to the use of
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
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
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)
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Contenido relacionado

PEPPSI-IPent catalyst

Pd-PEPPSI™-IPent is used for a variety of cross-coupling reactions.

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