Iodine(III) Reagent‐Mediated Intramolecular Amination of 2‐Alkenylanilines to Prepare Indoles

Abstract A 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 m CPBA. Furthermore, the indolo[3,2‐a]carbazole scaffold was prepared in good yield in six steps from commercial ortho ‐iodoaniline. magnified image