Tetrachlorophthalimides as Organocatalytic Acceptors for Electron Donor-Acceptor Complex Photoactivation

Excitation of photoactive electron donor-acceptor (EDA) complexes is an effective way to generate radicals.Applications in a catalytic regime typically use catalytic donors. Herein, we report that readily available electron-poortetrachlorophthalimides can act as effective organocatalytic acceptors to trigger the formation of EDA complexes with a variety ofradical precursors not amenable to previous catalytic methods. Excitation with visible light generates carbon radicals under mildconditions. The versatility of this EDA complex catalytic platform allowed us to develop mechanistically distinct radical reactions,including in combination with a cobalt-based catalytic system. Quantum yield measurements established that a closed catalytic cycleis operational, which hints at the ability of tetrachlorophthalimides to readily turn over and govern each catalytic cycle

Automated summary

In this study, it was found that tetrachlorophthalimides can act as effective organocatalytic acceptors, triggering radical reactions not amenable to previous catalytic methods. This finding allowed the development of mechanistically distinct radical reactions and the evaluation of catalytic cycle via quantum yield measurements.