Chemoselective Cu-catalyzed synthesis of diverse N-arylindole carboxamides, ß-oxo amides and N-arylindole-3-carbonitriles using diaryliodonium salts.

Chemoselective copper-catalyzed synthesis of diverse N-arylindole-3-carboxamides, ß-oxo amides and N-arylindole-3-carbonitriles from readily accessible indole-3-carbonitriles, α-cyano ketones and diaryliodonium salts has been developed. Diverse N-arylindole-3-carboxamides and ß-oxo amides were successfully achieved in high yields under copper-catalyzed neutral reaction conditions, and the addition of an organic base (DIPEA) resulted in a completely different selectivity pattern to produce N-arylindole-3-carbonitriles. Moreover, the importance of the developed methodology was realized by the synthesis of indoloquinolones and N-((1H-indol-3-yl)methyl)aniline and by a single-step gram-scale synthesis of the naturally occurring cephalandole A analogue.