CARBON-HYDROGEN FUNCTIONALIZATION OF 2-NAPHTHOL TO PREPARE ORGANOTELLURIUM AND ORGANOSELENIUM COMPOUNDS

Abstract

ABSTRACT Over the last decades, the chemistry of organoselenium and organotellurium compounds has brought the attention of the scientists and researchers fundamentally because of their biological importance and their useful activities in agrochemicals, insecticides, and drugs. Organoselenium compounds are known as chemical compounds that contain carbon-selenium chemical bond, while the organotellurium compounds are known chemical compounds containing carbon-tellurium chemical bond. Naphthyl phenyl selenides and naphthyl phenyl telluride are of much importance among all the types of organoselenium and organotellurium compounds due to their pharmaceutical applications. Therefore, efficient methods to synthesize naphthyl phenyl selenide compounds and naphthyl telluride compounds need to be developed. The functionalization of 2-naphthol has much importance due to its potential pharmaceutical and materials application. 2-Naphthol, also known as β-naphthol is a fluorescent colorless (or occasionally yellow) crystalline solid organic compound that is derived from naphthalene and belonging to the phenol family. In the present work, the synthesis of naphthyl phenyl selenide compounds and naphthyl phenyl telluride compounds was successfully achieved by the selenation and telluration of 2-naphthol using two different methods. The first synthetic method involves two steps: the synthesis of diaryl diselenides (ArSeSeAr) followed by the selenation reaction between ArSeSeAr and 2-naphthol promoted by I2. While the second method involves a one-pot three-component selenation reaction of 2-naphthol with elemental Se powder and aryl iodides (ArI) catalyzed by copper. The selenation and the telluration occur exclusively at the 1-position of 2-naphthol unit. The reaction conditions in this work were optimized using various chemical reaction conditions to achieve the best yields possible. The methods used in this research were found to be simple, efficient, and high yielding.