Selenomethoxylation of Alkenes Promoted by Oxone®

Gelson Perin, Paolo Santoni, Angelita M. Barcellos, Patrick C. Nobre, Raquel G. Jacob, Eder J. Lenardão, Claudio Santi

European Journal of Organic Chemistry · 2018 · 44 citations · 44 references

Concepts

Abstract

We describe herein an alternative method for the selenomethoxylation of unactivated alkenes using Oxone® as a stoichiometric oxidant. The electrophilic species of selenium were easily generated in situ by the reaction of diorganyl diselenides with Oxone®. By this efficient and simple approach, β‐methoxy‐selenides were obtained in moderate to excellent yields at room temperature in an open flask, starting from alkenes by using methanol as both nucleophile and solvent. When a mixture of H 2 O/CH 3 CN was employed as the solvent, β‐hydroxy‐selenides were selectively obtained under mild conditions.

References

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