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

Heteroarylcarboxamides containing a-nitrogens undergo copper-promoted N-phe nylation 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 ol-heteroatom chelating effec t is in the decreasing order of N>O, S. This discovery opens up the possibi lity of using other alpha -nitrogen functional groups to direct the N-aryla tion of peptides and simple amides under conditions as mild as that of amid e bond formation. (C) 2001 Dupont Pharmaceutical Company. Published by Else vier Science Ltd. All rights reserved.