One-Pot Conversion of Aromatic Bromides and Aromatics into Aromatic Nitriles

Various aromatic bromides and iodides were smoothly converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with butyllithium and subsequently DMF, followed by treatment with molecular iodine in aqueous ammonia. The same treatment of typical aromatics and heteroaromatics with butyllithium and subsequently DMF, followed by treatment with molecular iodine in aqueous ammonia also provided the corresponding aromatic nitriles in good yields. The present reactions are novel one-pot methods for the preparation of aromatic nitriles from aromatic bromides and aromatics, respectively, through the formation of aryllithiums and their DMF adducts.