Copper-Catalyzed Selective Arylations of Benzoxazoles with Aryl Iodides

A copper-catalyzed direct ring-opening
double N-arylation of benzoxazoles with aryl iodides
has been developed.
The present system exhibits high selectivity despite competition from C-arylation. The selectivity between ring-opening N-arylation and C-arylation was controlled
by the choice of reaction vessel. The nitrile bound bis­(triphenylphosphine)­copper
cyanide was identified as the active catalytic species for both reactions,
and when combined with a nitrile-containing solvent, enhanced the
reaction efficiency.