A 500 mL Schlenk flask was charged with 4,16-dibromo[2.2.]paracyclophane (1.50 g, 4.10 mmol, 1.00 equiv.) and dry THF (100 mL). The reaction mixture was cooled to –78 °C and n-BuLi (2.00 mL, 4.92 mmol, 1.20 equiv.) was added dropwise via syringe. The solution became pink in color and faded to a pale yellow. This step was allowed to proceed for 30 min. Then chlorodiphenylphosphine (1.51 mL, 1.81 g, 8.20 mmol, 2.00 equiv.) was added. The mixture was stirred overnight and allowed to warm slowly to room temperature. After the mixture was quenched with a saturated solution of NH4Cl, the mixture was extracted with ethyl acetate (3×50 mL). The organic layers were washed with brine, dried over MgSO4 and the solvents removed under reduced pressure. The residue was resolved in dichloromethane (100 mL) and H2O2 (35% aq. solution, 7.50 mL, 73.8 mmol, 18.0 equiv.) was added and stirred overnight.
