Mn(I)-Catalyzed Preferential Electrophilic C3-Maleimidation in Quinoxaline Leading to Spirocyclization and Dehydrogenation of Succinimides

A Mn-(I)-catalyzed site-selectivenondirected C3-maleimidation ofquinoxaline is established. Herein, the electrophilic C3-metalationprecedes over the o-directed strategy to access diverselysubstituted quinoxaline-appended succinimides. The products undergoPIFA-promoted C-(sp(2))-C-(sp(3)) spirocyclizationvia pi-electrons drifting from aryls and Selectfluor-mediateddehydrogenation of succinimide at room temperature.

Automated summary

A site-selective non-directed C3-maleimidation of quinoxaline is achieved through Mn-(I)-catalyzed reaction. The electrophilic C3-metalation is preferred over the o-directed strategy, leading to diversely substituted quinoxaline-appended succinimides. The products undergo PIFA-promoted C-(sp(2))-C-(sp(3)) spirocyclization via pi-electrons drifting from aryls and Selectfluor-mediated dehydrogenation of succinimide at room temperature.