Selective C(sp2)–H bond radical thiocyanation of cyclic α,β-unsaturated ketones†

Abstract

This study presents an AIBN catalyzed radical thiocyanation reaction, which efficiently enables the thiocyanation of C(sp²)–H bonds in cyclic conjugated unsaturated alkenes, such as uracil and quinolinone derivatives. The method demonstrates excellent substrate versatility, successfully synthesizing 5-thiocyanato derivatives of uracil and quinolinone compounds. It also shows remarkable tolerance to a wide range of functional groups, with yields ranging from 41% to 99%. Moreover, the reaction can be extended to other halogenation-based functionalization reactions, highlighting its practical applicability.