Abstract

A new and efficient method for the synthesis of lactones and esters involving the application of an molecular oxygen-based electro-catalytic oxidation system and ionic liquid [bmim][OTf] as electrolyte has been developed. The reaction between various ketones with molecular oxygen proceeds in a three-electrode cell under constant current conditions in [bmim][OTf] at room temperature to give the corresponding esters and lactones in good to excellent isolated yield. Additionally, the possible mechanism of Baeyer-Villiger oxidation of ketones in the electro-catalytic system is proposed. KEY WORDS : Baeyer-Villiger oxidation, Ketone, Molecular oxygen, Electrocatalysis, Ionic liquid Bull. Chem. Soc. Ethiop. 2016 , 30(2), 297-306. DOI: http://dx.doi.org/10.4314/bcse.v30i2.14

Highlights

  • Lactones and esters are important classes of chemicals that have been used extensively as synthetic intermediates in the preparation of a variety of fine or special chemicals such as drugs, steroids, pheromones, etc [1, 2]

  • A mixture of [bmim][OTf] (20 mL) and ketone (0.1 mol) in a three-electrode cell fitted with activated carbon fiber as the anode and Pt cathode was subjected to electro-catalytic oxidation at a constant current at room temperature for an appropriate time

  • Preliminary studies were performed using acetophenone as the model substrate on an activated carbon fiber (ACF) electrode in the presence of ionic liquid [bmim][OTf] electrolyte to examine the effects of various reaction parameters on the typical oxidation (Table 1)

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Summary

Introduction

Lactones and esters are important classes of chemicals that have been used extensively as synthetic intermediates in the preparation of a variety of fine or special chemicals such as drugs, steroids, pheromones, etc [1, 2]. A mixture of [bmim][OTf] (20 mL) and ketone (0.1 mol) in a three-electrode cell fitted with activated carbon fiber as the anode and Pt cathode was subjected to electro-catalytic oxidation at a constant current at room temperature for an appropriate time.

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