Synthesis of Phosphate Esters by Using Diphenyl Ditelluride as Organocatalyst

• Published in: European journal of organic chemistry 2023-04, Vol.26 (14), p.n/a
• Main Authors: Goulart, Helen A., Araujo, Daniela R., Iarocz, Lucas E. B., Pizzi, Bruna R., Barcellos, Thiago, Silva, Márcio S., Perin, Gelson
• Format: Article
• Language: English
• Subjects: Dehydrogenation; design of experiment; Esters; Factorial design; green chemistry; organocatalysis; Phosphates; Phosphonates; Phosphorylation; Spectrometry; Synthesis; ultrasonic irradiation
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202300021

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. 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.