Synthesis of Phosphate Esters by Using Diphenyl Ditelluride as Organocatalyst

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.

Automated summary

We developed a new synthetic method for the production of dialkyl(1-(organolthio)naphthalen-2-yl)phosphates and derivatives. This method involves a dehydrogenative phosphorylation reaction between functionalized naphthols and H-phosphonates, using diphenyl ditelluride as an organocatalyst and sonochemistry as an alternative energy source. The reaction conditions were optimized using factorial design approach, and under ultrasound irradiation, the desired products were obtained in yields ranging from 51-98% after 2 hours of sonication. The protocol also worked well with phenol and thiophenol starting materials.