Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light "on water".
A number of N-phenyl-1,4-naphthoquinone monoimines 6-10 were prepared by on-water oxidative phenylamination of 1,5-dihydroxynaphthalene (1) and 5-acetylamino-1-hydroxynaphthalene (5) with oxygen-substituted phenylamines under aerobic conditions and either solar or green LED radiation, in the presence of rose bengal as singlet oxygen sensitizer. As compared to the conventional oxidative phenylamination procedures, this novel synthetic method offers the advantage of aerobic conditions "on water" instead of hazardous oxidant reagents currently employed in aqueous alcoholic media.
Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique, Chile ; Instituto de Ciencias Exactas y Naturales (ICEN), Universidad Arturo Prat, Casilla 121, Iquique, Chile.
Julio
J
Benites
Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique, Chile.
Juan
J
Meléndez
Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique, Chile.
Cynthia
C
Estela
Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique, Chile.
David
D
Ríos
Facultad de Química, Universidad Técnica Federico Santa María, Casilla 110-V, Valparaíso, Chile.
Luis
L
Espinoza
Departamento de Química, Facultad de Ciencias Básicas Universidad de Antofagasta, Casilla 170, Antofagasta, Chile.
Iván
I
Brito
Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique, Chile ; Instituto de Ciencias Exactas y Naturales (ICEN), Universidad Arturo Prat, Casilla 121, Iquique, Chile.
Jaime A
JA
Valderrama
1,4-naphthoquinone monoimines; on water; oxidative coupling; rose bengal; solar radiation