Access to Benzyl Oxindoles via Electron Donor-Acceptor Complex Photoactivation Using Thianthrenium Salts and Potassium Carbonate

A photochemical synthesis of biologically relevant benzyl oxindoles is presented via electron-donor acceptor (EDA) complex strategy. This exogenous photocatalyst-free method describes the formation of a new electron donor-acceptor complex based on potassium carbonate and thianthrenium salts for C(sp2)-C(sp3) bond formation. This transition-metal free reaction allows a rapid increase in oxindoles molecular complexity chemical space, tolerating different functional groups as well as sophisticated biomolecules. The scalability and sustainability of this method is highlighted by an important waste recovery protocol. Mechanistic investigations support the formation of an EDA complex that induces a radical chain, and the applicability of this method is showcased by straightforward derivatization reactions. image