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900340

Sigma-Aldrich

rac-BINAP Pd G4

Sinonimo/i:

(Methanesulfonatato-κO)[2′-(methylamino-κN)-2-biphenylyl-κC2]palladium - 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphine)

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About This Item

Formula empirica (notazione di Hill):
C58H47NO3P2PdS
Numero CAS:
1599466-90-6
Peso molecolare:
1006.43
Codice UNSPSC:
12161600
ID PubChem:
329769806
NACRES:
NA.22

Forma fisica

powder

Livello qualitativo

100

Caratteristiche

generation 4

Impiego in reazioni chimiche

reaction type: Buchwald-Hartwig Cross Coupling Reaction
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
reaction type: Cross Couplings

Gruppo funzionale

phosphine

InChI

1S/C44H32P2.C13H12N.CH4O3S.Pd/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38;1-14-13-10-6-5-9-12(13)11-7-3-2-4-8-11;1-5(2,3)4;/h1-32H;2-7,9-10,14H,1H3;1H3,(H,2,3,4);/q;;;+1/p-1
JCAKNOAUMBTXEM-UHFFFAOYSA-M

Applicazioni

A powerful ligand for classic cross-coupling reactions combined with the Buchwald Fourth Generation Palladacycle. Bench stable, soluble in most organic solvents.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Certificati d'analisi (COA)

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Organic letters, 18(16), 4128-4131 (2016-08-09)
A general method for the N-arylation of amino acid esters with aryl triflates is described. Both α- and β-amino acid esters, including methyl, tert-butyl, and benzyl esters, are viable substrates. Reaction optimization was carried out by design of experiment (DOE)

Articoli

G3 and G4 Buchwald Precatalysts

G3 and G4 Buchwald palladium precatalysts are the newest air, moisture, and thermally stable crossing-coupling complexes used in bond formation for their versatility and high reactivity.

Contenuto correlato

Buchwald Group – Professor Product Portal

The Buchwald group has developed a series of highly active and versatile palladium precatalysts and biarylphosphine ligands used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. The ligands are electron-rich, and highly tunable to provide catalyst systems with a diverse scope, high stability and reactivity. Furthermore, the new series of precatalysts are air-, moisture and thermally-stable and display good solubility in common organic solvents. The use of precatalysts ensures the efficient generation of the active catalytic species and allows one to accurately adjust the ligand:palladium ratio. The ligands, precatalysts and methodology developed in the Buchwald group are user friendly and have rendered previously difficult cross couplings reactions, much easier to achieve.

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