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

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

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

WILEY-V C H VERLAG GMBH

Año: 2023

1434-193X

Abstract: 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 ligh 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 yields (up to 86%).