(For a discussion, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457–2483.) 10-Benzyl-3-iodo-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene (375.3 mg, 1.0 mmol), potassium acetate (785 mg, 8.0 mmol) and phenyl boronic acid (183 mg, 1.5 mmol) were combined in 10/1 ethanol/H2O (5 mL). The mixture was degassed (3 vacuum/N2 cycles), treated with tetrakis(triphenylphosphine)palladium(0) (57.5 mg, 0.05 mmol) and warmed to 90° C. for 18 h. The reaction was cooled, diluted with H2O and extracted with Et2O (3×50 mL). The organic layer was washed with brine (50 mL), dried (MgSO4), filtered and concentrated to provide an oil (180 mg, 55%). (TLC 4% ethyl acetate/hexanes Rf 0.18). GCMS m/e 325 (M)+.
