Electrochemical Site‐Selective Alkylation of Tropones via Formal C(sp3)−C(sp2) Coupling Reaction

Abstract

AbstractThe first site‐selective electrochemical alkylation of tropones is realized by reacting 2‐acetoxytropones and redox‐active‐esters (RAEs). The electroreductive protocol enables the preparation of mono‐ and disubstituted tropones in high yields (up to 71%) under very mild conditions. Dedicated voltammetric measurements served for the identification of 2‐acetoxytropones as a class of valuable trapping agents of nucleophilic radical species and shed light on the whole mechanistic profile. Wide tolerance towards functional groups (27 examples) and application to late‐stage functionalization of a bioactive compound (i. e. Colchicine analogue), emphasize the synthetic impact of the present methodology.