Abstract
A practical and environmentally benign electrochemical oxidation of thioethers and thiols in a commercially-available continuous-flow microreactor is presented.
Highlights
Sulfoxide and sulfone moieties are widespread in a broad variety of functional organic molecules.1 These moieties have been incorporated in numerous pharmaceutical compounds (e.g. Esomeprazole, Dapsone, Sulmazole, Methionine sulfone and Ponazuril)2 and even in polymeric materials3 (Fig. 1)
A wide variety of oxidizing agents have been used, such as H2O2 in combination with metal catalysts,7 m-CPBA,8 NaIO4,9 CrO3,9 KMnO4 10 and dioxiranes.11. These strategies typically suffer from selectivity issues, e.g. overoxidation of the sulfoxide to the sulfone or oxidation of other functional groups within the molecule
In order to find the optimal conditions for the direct electrochemical oxidation of thioethers, the potentiostatic oxidation of thioanisole [1] was taken as a benchmark (Table 1)
Summary
An environmentally benign and selective electrochemical oxidation of sulfides and thiols in a continuous-flow microreactor†. A practical and environmentally benign electrochemical oxidation of thioethers and thiols in a commercially-available continuous-flow microreactor is presented. Water is used as the source of oxygen to enable the oxidation process. The oxidation reaction utilizes the same reagents in all scenarios and the selectivity is solely governed by the applied potential. The use of continuous flow allows the optimal reaction parameters (e.g. residence time, applied voltage) to be rapidly assessed, to avoid mass- and heat-transfer limitations and to scale the electrochemistry
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