Allylic and Allenylic Dearomatization of Indoles promoted by Graphene Oxide via Covalent Grafting Activation Mode

open9noThe site-selective allylative and allenylative dearomatization of indoles with alcohols is performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt% loading) as the promoter. Metal-free conditions, absence of stoichiometric additive, environmentally friendly conditions (H2O/CH3CN, 55 °C, 6 h), broad substrate scope (33 examples, yield up to 92%) and excellent site- and stereoselectivity characterize the present methodology. Moreover, a covalent activation model exerted by GO functionalities was corroborated by spectroscopic, experimental and computational evidences. Recovering and regeneration of the GO catalyst via simple acidic treatment was also documented.PRIN‐2017 2017W8KNZWpartially_openembargoed_20210427Lorenzo Lombardi, Daniele Bellini, Andrea Bottoni, Matteo Calvaresi, Magda Monari, Alessandro Kovtun, Vincenzo Palermo, Manuela Melucci, Marco BandiniLorenzo Lombardi, Daniele Bellini, Andrea Bottoni, Matteo Calvaresi, Magda Monari, Alessandro Kovtun, Vincenzo Palermo, Manuela Melucci, Marco Bandin