Palladium-Catalyzed Kumada-Tamao-CorriuCross-Couplings

General Procedure for the Reaction of Aryl Chlorides with Grignard Reagents

A 50 mL of reactor was charged with 25.0 mg (0.05 mm) of POPd, 1.43 g (10.0 mm) of 4-chloroanisol and 10.0 mL of THF. The resulting mixture was stirred when addition of 15 mL (15.0 mm, 1.0 M in THF) of O-tolylmagnesium chloride at room temperature over a period of 5 min. The resulting mixture was stirred at room temperature for 4 h before the reaction was quenched with 10.0 mL of H2O, and the mixture was diluted with 300 mL of Et2O. After separation of organic and aqueous phases, the organic phase was washed with 50 mL of H2O, and 50 mL of brine, then dried over MgSO4, filtered and concentrated by rotary evaporation. The crude product was purified by column chromatography on silica gel using t-butylmethylether/hexane (1% volume ratio) to afford 1.72 g (87% yield) of 4-(o-tolyl)anisole.