Electrooxidation-induced synthesis of 3-thio/selenophosphorylated imidazole: a potent pesticide with good biocompatibility

Abstract

The development of convenient and practical synthetic strategies for constructing bioactive molecules without metal residues is of great interest in organic synthesis. Herein, a metal-free, operationally simple, and scalable electrooxidation-induced three-component cross-coupling method to access 3-thio/selenophosphorylated imidazole derivatives from readily available isothiocyanates/isoselenocyanates, isocyanates, and H-phosphonates is first reported. More than 30 examples have been provided with good to moderate yields. Importantly, the readily accessible compounds could be used as pesticides (wheat anti-locust) with good biocompatibility (5d-stimulated RAW 264.7 macrophages, IL-6 = 5.3 pg mL⁻¹, THF-α = 79.8 pg mL⁻¹), reiterating the importance of the developed electrochemical methodology.