Síntese de 2-organosselanil-naftalenos promovida por Oxone® e ultrassom

Abstract

In the present work, a methodology was developed based on the reaction of diaryl diselenides 1 with alkynols 2 to synthesize 2-organoselenyl- naphthalene 3. The electrophilic species were generates in situ, from oxidative cleavage of the Se–Se bond in diaryl diselenides by Oxone® using water as the solvent. These reactions proceeded efficiently under ultrasonic radiation using a range of diselenides and alkynols, both containing electron-withdrawing and electron-donating groups. Thus, afforded the corresponding 2-organoselenyl naphthalenes 3 in good yields (56-86%) and the reaction times ranged from 0.25 to 2.3 h, nine examples were obtained using ultrasonic irradiation and oxone® for the generation of electrophilic species of selenium and water as solvent. The diorganoyl diselenide used had the C6H5, 4-ClC6H4, 4-FC6H4, 2,4,6-(CH3)3C6H2, Py, C7O2H11 and the alkynols had the substituents C6H5, 4- ClC6H4, 4-CH3C6H4 e C3H7.