49 / 2023-08-14 11:09:25

Electrochemical Cross-Dehydrogenative Coupling Aromatic Amines: An Efficient Access to (Thio)Phosphamide

electrochemical; phosphamide; thiophosphamide; aromatic amine

New Technologies in Phosphorus Chemistry > 1) New reagents and methods in organophosphorus Chemistry

Organophosphorus amides can be used as potential phosphorus ligands in organic synthesis, which are also widely used in pesticides, medicinal chemistry, and material science. In addition to traditional methods,^[1] the cross-dehydrogenative coupling reaction provides another way to construct the P‒N bond,^[2-4] and the electrochemical strategy is continuously drawing the attention from organic chemists. To date, there are some pioneering works to realize the direct N‒H/P‒H cross-dehydrogenative coupling by using the electron as a clean and traceless oxidant, and a series of phosphamide derivatives have been successfully obtained. However, the nitrogen-based nucleophiles in the electrochemical manners are limited to primary alkyl amines,^[5] secondary alkyl amines^[6] and secondary aryl amines,^[7-8] and there is no report for the synthesis of thiophosphamides. Therefore, it is necessary to develop a new electrochemical system to construct P(O)‒N and P(S)‒N bonds for primary aryl amines in a green way.