Visible-Light-Driven Synthesis of Phenanthridin-6(5H)-one and N-Substituted Carbazole Derivatives through Intramolecular C-H Arylation

CUELLAR, MICAELA AYELÉN; MICAELA DENISE HEREDIA; GUILLERMO BRARDA; SILVIA MARICEL BAROLO; EVA DANIELA DÍAZ VÁZQUEZ; PAULA MARINA UBERMAN; SANDRA ELIZABETH MARTÍN; MARÍA EUGENIA BUDÉN

European Journal of Organic Chemistry

John Wiley and Sons Inc

Año: 2023 vol. 26

A visible-light-driven approach towards phenanthridin- 6(5H)-one and carbazole rings synthesis under transition-metal-free conditions is here reported. Phenanthridinones and carbazoles are synthesized through an intramolecular arylation of the corresponding N-(2-halobenzyl)-N-methylanilines or N-substituted-N-phenyl anilines using KOtBu as base in dimethyl sulfoxide (DMSO) at room temperature (rt), employing blue light emitting diodes (LEDs) as the light source. The reaction proceeds through photo- and basepromoted homolytic aromatic substitution via photoinduced electron transfer mechanism and it exhibits good tolerance to different functional groups, resulting in good to very good yields (up to 86%).