Artículo
Visible Light Mediated Synthesis of 6H-Benzo[c]chromenes: Transition-Metal-Free Intramolecular Direct C-H Arylation
Fecha de publicación:
01/2022
Editorial:
Royal Society of Chemistry
Revista:
Organic & Biomolecular Chemistry
ISSN:
1477-0520
e-ISSN:
1477-0539
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
A synthetic approach towards the 6H-benzo[c]chromene ring under visible light and transition-metal-free conditions has been developed. Benzochromenes are synthesized from the corresponding (2-halobenzyl) phenyl ethers or (2-halophenyl) benzyl ethers using KOtBu in dimethyl sulfoxide (DMSO) at room temperature (rt) and blue light-emitting diodes (LEDs) as the light source. This methodology replaces the use of ligands or additives, high temperatures and toxic solvents. The photostimulated reaction exhibits very good tolerance to different functional groups and 5H-dibenzo[c,f]chromenes are also effectively obtained. An electron donor-acceptor complex formed by the dimsyl anion and (2-halobenzyl) phenyl ethers was found and it induces the ET as the initial step in the photocyclization reaction. Furthermore, in order to explain the regiochemical outcome of this reaction, a theoretical analysis was performed using DFT methods.
Palabras clave:
Heterociclos
,
Fotoquímica
,
Luz visible
Archivos asociados
Licencia
Identificadores
Colecciones
Articulos(INFIQC)
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Citación
Heredia, Micaela Denise; Puiatti, Marcelo; Rossi, Roberto Arturo; Buden, Maria Eugenia; Visible Light Mediated Synthesis of 6H-Benzo[c]chromenes: Transition-Metal-Free Intramolecular Direct C-H Arylation; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 20; 1; 1-2022; 228-239
Compartir
Altmétricas