Dibenzoylperoxide-Mediated Oxidative α-Thio/Seleno-Cyanation of β-Ketoesters and Oxindoles

We herein report a protocol for the alpha-thio- and alpha-seleno-cyanation of different cyclic beta-ketoesters and oxindoles by using NaSCN or KSeCN as easily accessible inorganic nucleophilic S(e)CN sources under oxidative conditions. Key to success for both transformations is the use of dibenzoylperoxide as an oxidant allowing for the coupling of two inherently nucleophilic species under operationally simple conditions in high yields and with broad functional group tolerance.

Automated summary

We have developed a protocol for the alpha-thio- and alpha-seleno-cyanation of cyclic beta-ketoesters and oxindoles using NaSCN or KSeCN as inorganic nucleophilic S(e)CN sources. The key to the success of this transformation is the use of dibenzoylperoxide as an oxidant, enabling the coupling of two nucleophilic species under simple operation conditions with high yields and broad functional group tolerance.