Lewis-Acid-Catalyzed Selective Friedel-Crafts Reaction or Annulation between Anilines and Glyoxylates

A Lewis-acid-catalyzed selective reaction between anilines and glyoxylates was developed for synthesis of diarylmethanes or oxoimidazolidines. Under the catalysis of AgOTf, a series of anilines-based diarylmethanes, including primary, secondary, and tertiary anilines, were obtained in moderate to good yields. Moreover, stereoselective oxoimidazolidines were performed with the catalysis of Cu(OAc)(2)center dot H2O.

Automated summary

A Lewis acid-catalyzed selective reaction for the synthesis of diarylmethanes or oxoimidazolidines from anilines and glyoxylates was developed. The reaction yielded a series of aniline-based diarylmethanes and stereoselective oxoimidazolidines, depending on the catalyst used.