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An unprecedented <i>N</i>-alkylation of 3-nitroindoles with <i>para</i>-quinone methides was developed for the first time. Using potassium carbonate as the base, a wide range of structurally diverse <i>N</i>-diarylmethylindole derivatives were obtained with moderated to good yields via the protection group migration/<i>aza</i>-1,6-Michael addition sequences. The reaction process was also demonstrated by control experiments. Different from the previous advances where 3-nitrodoles served as electrophiles trapping by various nucleophiles, the reaction herein is featured that 3-nitrodoles is defined with latent <i>N</i>-centered nucleophiles to react with <i>ortho</i>-hydrophenyl <i>p</i>-QMs for construction of various <i>N</i>-diarylmethylindoles.