α-Nitrogen activating effect in the room temperature copper-promoted N-arylation of heteroarylcarboxamides with phenyl siloxane or p-toluylboronic acid

Heteroarylcarboxamides containing α-nitrogens undergo copper-promoted N-phenylation with hypervalent phenyl trimethylsiloxane at room temperature, in the absence of base and in air. Arylboronic acid can substitute for phenyl trimethylsiloxane as the organometalloid. The α-heteroatom chelating effect is in the decreasing order of N>O, S. This discovery opens up the possibility of using other α-nitrogen functional groups to direct the N-arylation of peptides and simple amides under conditions as mild as that of amide bond formation.