Ipso-amidation of arylboronic acids: Xenon difluoride-nitriles as efficient reagent systems

The xenon difluoride-mediated, ipso-amidation of boronic acids has been achieved for the first time under mild conditions. This method provides a simple, one-pot procedure for the direct synthesis of a series of anilides from the corresponding arylboronic acids and alkyl/aryl nitriles. Arylboronic acids bearing electron donating groups gave anilides in high yields, while moderate yields were observed for those bearing electron withdrawing groups. A plausible mechanism involving the formation of an aryl radical cation through single electron transfer by xenon difluoride, followed by the nucleophilic addition of the nitrile, is proposed.