902284

TyrannoPhos

• Synonym(s): Cyclopentylbis(3,5-di-tert-butylphenyl)phosphine, Phosphine ligand for nickel catalysis
• Empirical Formula (Hill Notation): C₃₃H₅₁P
• CAS Number: 2097604-70-9
• Molecular Weight: 478.73
• MDL number: MFCD32068357
• UNSPSC Code: 12161600
• NACRES: NA.22

Properties

• form: powder or crystals
• reaction suitability: 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
• functional group: phosphine
• SMILES string: CC(C1=CC(P(C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2)C3CCCC3)=CC(C(C)(C)C)=C1)(C)C
• InChI: 1S/C33H51P/c1-30(2,3)23-17-24(31(4,5)6)20-28(19-23)34(27-15-13-14-16-27)29-21-25(32(7,8)9)18-26(22-29)33(10,11)12/h17-22,27H,13-16H2,1-12H3
• InChI key: IWPJBOKLLTVJMY-UHFFFAOYSA-N

Description

Application

This new aryl alkylphosphine ligand developed in Abby′s Doyle′s lab has been tailored specifically for nickel catalysis as demonstrated in the Suzuki coupling of acetals with boronic acids to generate benzylic ethers, reactions that pose challenges in Ni catalysis when using phosphine ligands developed for Pd-catalysed couplings.

Other Notes

Parameterization of phosphine ligands demonstrates enhacement of nickel catalysis via remote steric effects

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable