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804355

Sigma-Aldrich

BrettPhos Pd G4

Sinonimo/i:

(SP-4-3)-[Dicyclohexyl[3,6-dimethoxy-2′,4′,6′-tris(1-methylethyl)[1,1′-biphenyl]-2-yl]phosphine-κP](methanesulfonato-κO)[2′-(methylamino-κN)[1,1′-biphenyl]-2-yl-κC]

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About This Item

Formula empirica (notazione di Hill):
C49H68NO5PPdS
Numero CAS:
Peso molecolare:
920.53
Numero MDL:
Codice UNSPSC:
12161600
ID PubChem:
NACRES:
NA.22

Saggio

95%

Livello qualitativo

Stato

powder

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

Stringa SMILE

CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C(OC)=CC=C2OC.CNC5=C(C6=C([Pd]OS(C)(=O)=O)C=CC=C6)C=CC=C5

InChI

1S/C35H53O2P.C13H12N.CH4O3S.Pd/c1-23(2)26-21-29(24(3)4)33(30(22-26)25(5)6)34-31(36-7)19-20-32(37-8)35(34)38(27-15-11-9-12-16-27)28-17-13-10-14-18-28;1-14-13-10-6-5-9-12(13)11-7-3-2-4-8-11;1-5(2,3)4;/h19-25,27-28H,9-18H2,1-8H3;2-7,9-10,14H,1H3;1H3,(H,2,3,4);/q;;;+1/p-1
YVIWYUQZBYFFLZ-UHFFFAOYSA-M

Descrizione generale

BrettPhos Pd G4 is an N-substituted 2-aminobiphenylpalladium methanesulfonate precatalyst. It is a fourth generation (G4) Buchwald precatalyst that is similar to the third generation (G3) precatalysts except that the amino group on the biphenyl backbone is methylated. This modification helps to prevent the limitations of using the third generation precatalysts. It is air, moisture and thermally-stable and shows good solubility in common organic solvents. BrettPhos Pd G4 is highly useful in cross-coupling reactions. Some of its excellent features include lower catalyst loadings, shorter reaction time, efficient formation of the active catalytic species and accurate control of ligand: palladium ratio.

Applicazioni

  • High Throughput Experimentation in Pharmaceutical Process Chemistry: This study evaluates the efficacy of BrettPhos Pd G4 in a ring closure reaction, emphasizing its selectivity and yield, which supports its potential utility in pharmaceutical synthesis (Solazzo, 2022).
  • Synthesis and characterization of fluorescent amino acid dimethylaminoacridonylalanine: Research detailing the use of various Buchwald precatalysts including BrettPhos Pd G4. The study explores the synthesis of a fluorescent amino acid, highlighting the specific conditions where BrettPhos Pd G4 provided notable benefits over other catalysts (Jones et al., 2021).

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


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Slide 1 of 10

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N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C?C and C?N Cross-Couplings.
Bruno NC, et al.
The Journal of Organic Chemistry, 79(9), 4161-4166 (2014)

Articoli

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.

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