Organochalcogenation of 2-naphthol derivatives promoted by I2/TBHP: a suitable and metal-free approach to the synthesis of 1-(organochalcogenyl)naphthalen-2-ols

In this work, we present an efficient and metal-free protocol for the synthesis of chalcogen-functionalized 2-naphthol derivatives through electrophilic aromatic substitution (EAS) reactions between 2-naphthols and diorganyl dichalcogenides. The reactions are mediated by an oxidative system composed of molecular iodine and tert-butyl hydroperoxide (I2/TBHP), which enables the in situ generation of electrophilic chalcogen species, in ethanol as a green solvent. Under these conditions, eleven selenium-based naphthols were obtained at room temperature within 1 h, with isolated yields ranging from 35% to 94%. Additionally, seven sulfur analogues were obtained in yields of 65% to 85%, after 24 h of reaction at 80 °C.