RuPhos Pd G3

Synthesis

mixture of μ-OMs dimer Et₂O (a 1:1 complex characterized by 1H NMR) (0.5 equivalents, 0.871 g, 1.071 mmol), 1,1'-(diphenylphosphino)ferrocene (1.0 equivalents, 1.2 g, 2.141 mmol), and anhydrous THF (15.0 mL) was stirred at room temperature under an argon atmosphere for 1 hour. The solvent was removed under vacuum. The crude product was treated with n-pentane (75.0 mL) as a triurate. The resulting mixture was dried under vacuum for 24 hours to give the product RuPhos Pd G3.

Figure: Synthetic route of RuPhos Pd G3">

Synthetic route of RuPhos Pd G3

Reaction

1. Palladium catalyst used for facile, C-N cross-coupling reactions.
2. A practical synthesis of indoles via a Pd-catalyzed C-N ring formation.

Uses

RuPhos Pd G3 can be used as a pre-catalyst in the following protocols:

• Palladium-catalyzed Suzuki coupling of 5-p-toluenesulfonyltetrazoles with arylboronic acids to synthesize 1,5-disubstituted tetrazoles.
• Suzuki-Miyaura catalyst-transfer polycondensation (SCTP) of 3-alkylthiophenes in the presence of N-methylimidodiacetic (MIDA)-boronate monomers.
• Suzuki-Miyaura-cross-coupling of aminothiophenes.

General Description

RuPhos Pd G3 is a third generation (G3) Buchwald precatalyst that can be used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. It is air-, moisture-, and thermally-stable and is highly soluble in a wide range of common organic solvents. Some of its unique features include lower catalyst loadings, shorter reaction time, efficient formation of the active catalytic species and accurate control of ligand: palladium ratio.

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings