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

Author:

Cuellar Micaela Ayelén12ORCID,Heredia Micaela Denise12ORCID,Brarda Guillermo12ORCID,Barolo Silvia Maricel12ORCID,Vázquez Eva Daniela Díaz12ORCID,Uberman Paula Marina12ORCID,Martín Sandra Elizabeth12ORCID,Budén María Eugenia12ORCID

Affiliation:

1. Departamento de Química Orgánica Facultad de Ciencias Químicas Universidad Nacional de Córdoba

2. Instituto de Investigaciones en Fisicoquímica de Córdoba-INFIQC-CONICET Universidad Nacional de Córdoba Haya de La Torre y Medina Allende Ciudad Universitaria X5000HUA Córdoba Argentina

Abstract

AbstractA 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 base‐promoted 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 %).

Funder

Consejo Nacional de Investigaciones Científicas y Técnicas

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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