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804355

Sigma-Aldrich

BrettPhos Pd G4

Sinônimo(s):

(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

Fórmula empírica (Notação de Hill):
C49H68NO5PPdS
Número CAS:
Peso molecular:
920.53
Número MDL:
Código UNSPSC:
12161600
ID de substância PubChem:
NACRES:
NA.22

Ensaio

95%

Nível de qualidade

Formulário

powder

Características

generation 4

adequação da reação

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

grupo funcional

phosphine

cadeia de caracteres SMILES

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

chave InChI

YVIWYUQZBYFFLZ-UHFFFAOYSA-M

Descrição geral

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.

Aplicação

  • 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).

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


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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)

Artigos

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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