Iron-Catalyzed Metal-Ligand Cooperative Approach toward Sustainable Synthesis of Azines and N-Acylhydrazones in Air

Herein, we describe a metal-ligand cooperative approach for the sustainable synthesis of various aldazines, ketazines, and N-acylhydrazones via dehydrogenative functionalization of alcohols with hydrazine hydrate using a simple, easy-to-prepare iron catalyst featuring a redox noninnocent tridentate arylazo backbone. Our catalyst is compatible with both primary and secondary alcohols to produce a wide variety of substituted aldazines, ketazines, and N-acylhydrazones in good isolated yields in air. A series of control experiments are performed to elucidate the reaction mechanism.

Automated summary

Here, we report a metal-ligand cooperative approach for the sustainable synthesis of various aldazines, ketazines, and N-acylhydrazones through the dehydrogenative functionalization of alcohols with hydrazine hydrate using a simple iron catalyst featuring a redox noninnocent tridentate arylazo backbone. The catalyst is compatible with both primary and secondary alcohols, yielding a wide variety of substituted aldazines, ketazines, and N-acylhydrazones in good isolated yields in air. Control experiments are conducted to elucidate the reaction mechanism.