Synthesis of Phosphate Esters by Using Diphenyl Ditelluride as Organocatalyst

This work demonstrates an approach to prepare phosphate esters by a dehydrogenative phosphorylation reaction between functionalized naphthols and H-phosphonates using diphenyl ditelluride as an organocatalyst and sonochemistry as an alternative energy source. The method was also suitable to the use α-naphthol, β-naphthol, phenol and thiophenol.

Abstract

We report a protocol for the synthesis of new dialkyl(1-(organolthio)naphthalen-2-yl)phosphates and derivatives via a dehydrogenative phosphorylation reaction between functionalized naphthols and H-phosphonates. Diphenyl ditelluride was employed as an organocatalyst and sonochemistry as an alternative energy source. The reaction conditions were defined through a factorial design approach, and the best condition provided the synthesis of dialkyl(1-(organolthio)naphthalen-2-yl)phosphates in yields that varied from 51–98 % under ultrasound irradiation after 2 h of sonication. The synthetic protocol was also effective for phenol and thiophenol starting materials. All products were characterized by state-of-the-art spectroscopic and spectrometric techniques.

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