Iron-Catalyzed Trifluoromethylation of Indole-Tethered Alkene Enables Synthesis of CF3-Containing Spiroindolenines and Tetrahydrocarbazoles

An iron-catalyzed trifluoromethylation of indole-tethered alkene with Togni's reagent to construct CF3-containing spiro[indole-3,3 '-pyrrolidine] and tetrahydrocarbazole derivatives under mild and convenient conditions has been disclosed. Mechanistic studies indicate that the reaction proceed through a CF3 radical addition to the alkene, followed by sequential dearomatizing spiocyclization of the indole and oxidation to afford the spiro[indole-3,3 '-pyrrolidine] derivatives. Meanwhile, when the substituent at the C2 position of the indole is hydrogen, the CF3-containing tetrahydrocarbazole is obtained through trifluoromethylation of alkene and cyclization of indole.