3‑Alkenylation or 3‑Alkylation of Indole with Propargylic Alcohols: Construction of 3,4-Dihydrocyclopenta[b]indole and 1,4-Dihydrocyclopenta[b]indole in the Presence of Different Catalysts

3-Alkenylation or 3-alkylation of indole with propargylic alcohols could be efficiently controlled by the catalyst. In the presence of triflic acid, 3-alkenylation of indole occurred and a 3,4-dihydrocyclopenta­[b]­indole skeleton was effectively constructed in moderate to excellent yields via a cascade process. In the presence of Cu­(OTf)2, 3-alkylation of indole resulted in the formation of 3-propargylic indole, which could be further converted into 2-iodo-1,4-dihydrocyclopenta­[b]­indoles in the presence of N-iodosuccinimide and boron trifluoride etherate. Possible mechanisms related to the 3-alkenylation or 3-alkylation of indole and their extension to the formation of 3,4-dihydrocyclopenta­[b]­indoles or 1,4-dihydrocyclopenta­[b]­indoles are postulated and discussed.