901906

2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

95%

• Synonym(e): S-Phos, SPhos
• Empirische Formel (Hill-System): C₂₆H₃₅O₂P
• CAS-Nummer: 657408-07-6
• Molekulargewicht: 410.53
• MDL-Nummer: MFCD05861611
• UNSPSC-Code: 12161600
• NACRES: NA.22

Eigenschaften

• Assay: 95%
• Form: powder or crystals
• Eignung der Reaktion: 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; reagent type: ligand
• mp (Schmelzpunkt): 164-166 °C (lit.); 165.5 °C
• Funktionelle Gruppe: phosphine
• SMILES String: COc1cccc(OC)c1-c2ccccc2P(C3CCCCC3)C4CCCCC4
• InChI: 1S/C26H35O2P/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21/h9-11,16-21H,3-8,12-15H2,1-2H3
• InChIKey: VNFWTIYUKDMAOP-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

SPhos [2-Dicyclohexylphosphino-2′, 6′-dimethoxybiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

Anwendung

SPhos may be used as a ligand in the following processes:

• Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between Boc-protected aminomethyltrifluoroborate and aryl chlorides or hetaryl chlorides to form the corresponding aminomethylarenes.
• Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between 4-methyl-substituted piperidinylzinc reagent and different aryl or heteroaryl iodides to form various substituted piperidines.
• Intramolecular Suzuki-Miyaura coupling to form the 18-membered macrocyclic ring during the multi-step synthesis of riccardin C.

Utilized in conjunction with palladium to form a highly active catalyst for C-N bond formation

Universell genutzter Ligand für die Suzuki-Miyaura-Kupplung; Arylchloride, gehinderte Biaryle, Heterobiaryle.

Rechtliche Hinweise

Verwendung unterliegt Patenten: US 6307087; EP 1097158; JP 5758844; CA 2336691

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable