Photoredox initiated azole-nucleophilic addition: oxo-azolation of gem-difluoroalkenes

A mild and general protocol for photoredox initiated oxo-azolation of gem-difluoroalkenes has been demonstrated. The reaction strategy offers a facile access to a series of synthetically useful azolated difluoroacetonarenes that may have significant applications in drug and functional materials development. The reaction also tolerates a wide range of functional groups for further manipulation. In addition, a preliminary mechanistic study indicated a photoredox initiated, active oxygen participated single electron transfer pathway for the reaction. Finally, the reaction solvent could be easily recovered and reused with the same reaction efficiency.

Automated summary

This study demonstrates a mild and general protocol for the photoredox initiated oxo-azolation of gem-difluoroalkenes, providing a facile access to synthetically useful azolated difluoroacetonarenes with potential applications in drug and functional materials development. The reaction tolerates a wide range of functional groups and involves a photoredox initiated, active oxygen participated single electron transfer pathway. Furthermore, the reaction solvent can be easily recovered and reused with the same efficiency.