Electrooxidation-induced synthesis of 3-thio/selenophosphorylated imidazole: a potent pesticide with good biocompatibility
GREEN CHEMISTRY(2024)
摘要
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-alpha = 79.8 pg mL-1), reiterating the importance of the developed electrochemical methodology. A facile and scalable electrooxidation-induced three-component cross-coupling strategy has been first disclosed for accessing 3-thio/selenophosphorylated imidazoles, which exhibit promising biocompatible pesticides.
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