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732117

Sigma-Aldrich

Pd-PEPPSI™-IPent catalyst

≥95%

Synonyme(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

Formule empirique (notation de Hill):
C40H56Cl3N3Pd
Numéro CAS:
1158652-41-5
Poids moléculaire :
791.67
Code UNSPSC :
12161600
ID de substance PubChem :
329764705
Nomenclature NACRES :
NA.22

Niveau de qualité

200

Pureté

≥95%

Forme

solid

Pertinence de la réaction

core: palladium
reagent type: catalyst

Capacité de réaction

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

Pf

195-201 °C

Température de stockage

−20°C

Chaîne 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

Clé InChI

BCXSKTXOKALLAZ-UHFFFAOYSA-L

Description générale

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)

Informations légales

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302 + H312 + H332

Classification des risques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Faites votre choix parmi les versions les plus récentes :

Certificats d'analyse (COA)

Lot/Batch Number
MKCV5086
MKCV1774
MKCV3842
MKCW0308
MKCW0307

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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
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)
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
Afficher tous les articles scientifiques apparentés

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.

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 Kit

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

KitAlysis™ Suzuki-Miyaura Cross-Coupling Kit

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

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