Seal the resealable reaction tube containing the magnetic follower with a rubber septum. Dry the tube with a flame under an argon atmosphere. Add tBu3P·HBF4 (10.9 mg, 0.0377 mmol) and Pd2(dba)3 (17.3 mg, 0.0189 mmol) to the tube. Dissolve aryl bromide (83.6 mg) in anhydrous toluene (0.9 mL). Add the resulting solution to the tube using a syringe. Add tert-butyl acetate (87.6 mg) to the tube. Cool the reaction mixture to -78°C. Degas the reaction mixture with argon for 15 min.
Add degassed LiHDMS solution (0.942 mL, 1 M toluene solution) to the mixture using a syringe. Degause the reaction mixture for 15 minutes. Replace the rubber diaphragm with a screw cap. Stir the reaction mixture at room temperature for 16 hours. Quench the reaction by adding saturated NaHCO3 aqueous solution (25 mL). Extract the aqueous layer with Et2O (3 × 25 mL). Dry the combined organic matter with Na2SO4. Filter the combined organic matter. Remove the solvent under vacuum. Purify the product by rapid column chromatography [petroleum/EtOAc 50:1, fractionated to 5:1].
