Electrochemical Regioselective C(sp2)-H Bond Chalcogenation of Pyrazolo[1,5-a]pyrimidines via Radical Cross-Coupling at Room Temperature

Abstract

Herein, we disclose an electrochemical approach for the C(sp2)-H chalcogenation of pyrazolo[1,5-a]pyrimidines. This technique offers an oxidant and catalyst-free protocol for achieving regioselective chalcogenation of pyrazolo[1,5-a]pyrimidines. The procedure uses only 0.5 equiv. of diaryl chalcogenides which underscores the atom economy of the protocol. Key attributes of this methodology include mild reaction conditions, short reaction time, utilization of cheap electrode materials, and eco-friendly reaction conditions. Cyclic voltammetry studies and radical quenching experiments revealed a radical cross-coupling pathway for the reaction mechanism. © 2024 American Chemical Society.