A 4-mL vial was charged with bromobenzene (63 mg, 0.40 mmol), Pd(dba)2 (11.5 mg, 0.0200 mmol), Ph5FcP-(t-Bu)2 (14.2 mg, 0.0200 mmol), and sodium tert-butoxide (47 mg, 0.48 mmol). Anhydrous toluene (2 mL) was added, and the vial was sealed with a cap containing a PTFE septum and removed from the dry box. The reaction mixture was stirred at room temperature for 23 h. The reaction solution was then adsorbed onto silica gel, and the product was isolated by eluting with EtOAc/hexanes (0 to 10% gradient) to give the ether (58 mg, 97%).
Reference: Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553–5566.
