Abstract

AbstractA variety of 3‐substituted and 2,3‐disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2‐alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3‐acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5‐dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2‐a]carbazole scaffold was prepared in good yield in six steps from commercial ortho‐iodoaniline.magnified image

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