Zur protonenkatalysierten elektrophilen substitution von 2,3-dimethylindol mit arylaldehyden: C6-regioselektivität am indol-gerüst

The proton catalyzed reaction of 2,3-dimethylindole (1) with several arylaldehydes 2 yields the 6,6′bisindolylarylmethanes 5 regioselectively. No mechanistic information about the predominant attack of the aldehydes on the indole nucleus is obtained, because the reaction proceeds too fast to control. The electron-rich aldehydes, 2,4,6-trimethoxybenzaldehyde and indole-3-carbaldehyde, yield exclusively the 6,6′,6″-trisin-dolylmethane 9. The constitutions of all isolated methanes were elucidated by 400 MHz 1H-nmr spectroscopy.