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732117

Sigma-Aldrich

Pd-PEPPSI™-IPent catalyst

≥95%

Sinônimo(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

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

Nível de qualidade

200

Ensaio

≥95%

Formulário

solid

adequação da reação

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

pf

195-201 °C

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

BCXSKTXOKALLAZ-UHFFFAOYSA-L

Categorias relacionadas

Descrição geral

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

Aplicação

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)

Informações legais

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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H302 + H312 + H332

Classificações de perigo

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

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
MKCQ9807
MKCQ4902
MKCP5796
MKCN9925
MKCN5524

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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)
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
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
Colin Chih-Chien Wu et al.
Molecular cell, 73(5), 959-970 (2019-01-29)
Ribosomes undergo substantial conformational changes during translation elongation to accommodate incoming aminoacyl-tRNAs and translocate along the mRNA template. We used multiple elongation inhibitors and chemical probing to define ribosome conformational states corresponding to differently sized ribosome-protected mRNA fragments (RPFs) generated
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Artigos

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

Professor Mike Organ at York University, along with co-workers Dr. Chris O’Brien and Dr. Eric Kantchev, have developed an palladium N-heterocyclic-carbene (NHC) catalyst system. They reacted PdCl2with a bulky NHC ligand, 2,6-diisopropylphenyllimidazolium chloride (IPr), and an α-donating 3-chloropyridine ligand for stability. The title complex, PEPPSI™, stands for Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation. Sigma-Aldrich offesr gram-scale quantities of the PEPPSI™ catalyst in collaboration with the Organ research group.

Scale-Up Guide: Suzuki-Miyaura Cross-Coupling Reaction

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form.

KitAlysis™ Suzuki-Miyaura Cross-Coupling Reaction Screening Kit

Multiple tools have been created to ensure your success with kit set up. Start with the more detailed guide to ensure you are comfortable with all of the steps before using the quick guides on the excel worksheet. Remember that while the technique is new, it is still organic chemistry and so the steps will seem easy once you try just one kit. It is just a new way of approaching something you are already very good at.

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