Electrochemical Selenocyanation and Thiocyanation of Azaindoles and Deazapurines

Abstract

An economical and regioselective electrochemical oxidative C─H selenocyanation or thiocyanation of N ‐rich heteroarenes, such as azaindole and deazapurine, is reported utilizing graphite electrodes. The reaction proceeds without the need for any catalyst or oxidant under a constant electric current in an undivided electrolytic cell. The commercially available reagents KSCN or KSeCN were used for the chalcogenocyanation reactions. A variety of selenocyanated and thiocyanated derivatives were synthesized in yields of 70%–90%, and the reactions also tolerated different electron‐rich or electron‐deficient substituents on the heterocyclic core.