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747130

Sigma-Aldrich

Josiphos SL-J009-1 Pd G3

Synonym(e):

Josiphos SL-J009-1-G3-palladacycle, {(R)-1-[(Sp)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine}[2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate

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About This Item

Empirische Formel (Hill-System):
C45H65FeNO3P2PdS
CAS-Nummer:
Molekulargewicht:
924.28
MDL-Nummer:
UNSPSC-Code:
12161600
PubChem Substanz-ID:
NACRES:
NA.22

Form

solid

Qualitätsniveau

Leistungsmerkmale

generation 3

Eignung der Reaktion

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

mp (Schmelzpunkt)

180-186 °C

Funktionelle Gruppe

phosphine

SMILES String

NC1=C(C=CC=C1)C2=C([Pd]OS(C)(=O)=O)C=CC=C2.C[C@@H](P(C(C)(C)C)C(C)(C)C)[C]3[C](P(C4CCCCC4)C5CCCCC5)[C][C][C]3.[C]6[C][C][C][C]6.[Fe]

InChI

1S/C27H47P2.C12H10N.C5H5.CH4O3S.Fe.Pd/c1-21(29(26(2,3)4)27(5,6)7)24-19-14-20-25(24)28(22-15-10-8-11-16-22)23-17-12-9-13-18-23;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-2-4-5-3-1;1-5(2,3)4;;/h14,19-23H,8-13,15-18H2,1-7H3;1-6,8-9H,13H2;1-5H;1H3,(H,2,3,4);;/q;;;;;+1/p-1/t21-;;;;;/m1...../s1

InChIKey

GJFJVCUFUWXFEB-RPDSBUJNSA-M

Allgemeine Beschreibung

Josiphos SL-J009-1 Pd G3 (Josiphos SL-J009-1-G3-palladacycle) is a modified G3 precatalyst (G3′). It has been synthesized by Buchwald and coworkers from second generation (G2) precatalyst by methylation of the amino group present on biphenyl backbone. It is a useful catalyst for various cross-coupling reactions. G3 precatalysts are versatile catalysts. They have long life in solution and are readily soluble in various organic solvents. G3- precatalysts have been employed in various C-N bond forming reactions.

Anwendung


  • Total Syntheses of N-Paspaline and N-Emindole PB: Discusses the use of various catalysts including RuPhos and Josiphos ligands for synthesizing complex molecular structures (Radical-Polar Crossover Cyclizations, 2020).

  • Unprotected Indazoles Are Resilient to Ring-Opening Isomerization: A Case Study on Catalytic C-S Couplings in the Presence of Strong Base: Utilizes Josiphos SL-J009-1 Pd-G3 for catalytic C-S coupling reactions under strong base conditions (The Journal of Organic Chemistry, 2017).

  • Synthesis and characterization of an isopropylBippyPhos precatalyst: Compares various phosphine ligands including XPhos and Josiphos for catalytic activity in organic syntheses (Tetrahedron, 2022).

  • Novel quorum sensing inhibitors targeting PqsR: Mentions the experimental use of Josiphos ligands in the synthesis of potential pharmaceutical compounds (2020, University of Saarland).

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

2-Aminobiphenyl Palladacycles: The ?Most Powerful? Precatalysts in C-C and C-Heteroatom Cross-Couplings.
Bruneau A, et al.
ACS Catalysis, 5(2), 1386-1396 (2015)

Artikel

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form. Once activated by base under the reaction conditions they become sensitive to air. To best enable scale-up success, the use of standard Schlenk technique is recommended.

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form. Once activated by base under the reaction conditions they become sensitive to air. To best enable scale-up success, the use of standard Schlenk technique is recommended.

All contents in the foil bag are weighed, plated, packed, and sealed in a glove box under nitrogen.

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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