Aerobic Oxidation of Phosphite Esters to Phosphate Esters by Using an Ionic-Liquid-Supported Organotelluride Reusable Catalyst

Abstract

We describe the synthesis of an ionic-liquid (IL)-supported organotelluride catalyst and its application as a recyclable catalyst for the aerobic oxidation of phosphite esters to phosphate esters. This method shows high conversion rates, allows the ready isolation and purification of the resulting products, and exhibits good reusability of the catalyst.

Keywords

organotellurides - ionic liquids - oxidation - phosphate esters - reusable catalysts - phosphite esters

Publication History

Received: 31 August 2020

Accepted after revision: 20 September 2020

Article published online:
16 October 2020

• References and Notes

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• 10 Triphenyl Phosphate (Table [2], Entry 1); Typical Procedure A solution of (PhO)₃P (0.0773 g, 0.250 mmol) in (bmim)[PF₆] (5 mL) containing 5 (0.0330 g, 0.0500 mmol) and rose bengal (0.0128 g, 0.0125 mmol) was vigorously stirred in an open flask and irradiated with a 60 W LED lamp for 2.5 h. The temperature was kept at about 15 °C by using an ice bath during the irradiation. The resulting mixture was extracted with Et₂O, and the solvent was then evaporated to give a pink solid; yield: 0.0803 g (99%); mp 44–47 °C.¹H NMR (500 MHz, CDCl₃): δ = 7.36 (t, J = 7.7, 6 H), 7.25–7.19 (m, 9 H). ¹³C NMR (125 MHz, CDCl₃): δ = 150.6, 150.5, 130.0, 125.7, 120.3, 120.2. ³¹P NMR (202 MHz, CDCl₃): δ = –17.7. HRMS (APCI): m/z [M + H]⁺ calcd for C₁₈H₁₆O₄P: 327.0781; found: 327.0743.