Selenofuncionalização de 2-naftóis utilizando ácidos arilselenínicos e glicerol como solvente verde

Abstract

In the present work, a new method based on the principles of green chemistry for the synthesis of 1-arylselanyl-naphthalen-2-ols was studied and elaborated. In which, a method for selenofunctionalization of naphthols was developed, using electrophilic species generated in situ, from arylseleninic acids and glycerol as an alternative solvent. Thus, nine compounds were obtained in satisfactory yields (62-85%) using a conventional reaction system, at a temperature of 70 °C, in an open flask and in short reaction times, between 0.25 and 1.0 h. These reactions occurred efficiently, using different arylseleninic acids, containing electron donor and withdrawn groups linked to the aromatic ring, such as the substituents: 4-CH3, 4-CH3O, 4-Cl, 4-F, 2,4,6-(CH3)3 and naphthila. The expansion of the reaction scope of the developed method can be extended to different arenes, being obtained nine compounds, in moderate to excellent yields (58-95%), with reaction times between 0.5 and 48.0 h. In addition, the developed method proved to be efficient for the selenofunctionalization of the drug Naproxen® and of the scale-up to 5.0 mmol, which enables the employability of this reaction in an industrial application. It was also possible to reuse glycerol in up to 7 reaction cycles, maintaining good efficiency, with moderate yields of 54 85%, corroborating with the goods results obtained in the evaluation of green chemistry metrics, obtaining a method with excellent atomic economy, a low E factor and an acceptable Eco scale.