Synthesis of Seven-Membered Azepino[3,2,1-<i>hi</i>]indoles via Rhodium-Catalyzed Regioselective C–H Activation/1,8-Diazabicyclo[5.4.0]undec-7-ene-Catalyzed Intramolecular Amidation of 7‑Phenylindoles in One Pot

An unprecedented rhodium-catalyzed regioselective C–H activation/1,8-diazabicyclo[5.4.0]­undec-7-ene-catalyzed intramolecular amidation of 7-arylindoles with diazomalonates is described that provides a straightforward route to seven-membered azepino­[3,2,1-hi]­indoles in good to excellent yields in one pot. A wide range of functional groups, including F, OMe, NPh2, SiMe3, Cl, CN, CHO, COMe, CO2Me, CF3, and NO2, were all well-tolerated.