Bromobenzene → Diphenylpyrrolidine

Participants

Reaction Conditions

Reaction Steps

Caesium carbonate (553 mg, 1.70 mmol) was added to bromobenzene (0.059 mL, 0.57 mmol) and 2-phenylpyrrolidine (100 mg, 0.68 mmol) in 1,4-dioxane (2 mL). The reaction was degassed and Tris(dibenzylideneacetone)?dipalladium(0) (12.96 mg, 0.01 mmol) and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (RuPhos) (13.21 mg, 0.03 mmol) were added. The resulting solution was stirred at 100 °C for 16 hours. LCMS showed the formation of the product. The reaction mixture was diluted with EtOAc, and washed with water. The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. NMR confirmed the presence of the product. The crude product was purified by flash silica chromatography, elution gradient 0 to 15% DCM in MeOH. Pure fractions were evaporated to dryness to afford 1,2-diphenylpyrrolidine (114 mg, 90 %) as a brown oil.

Provenance & Evidence