Electrochemical oxidative selenocyclization of olefinic amides towards the synthesis of iminoisobenzofurans

Organoselenium compounds are important structures in medicinal chemistry, materials chemistry and biochemistry. Many drugs contain heterocyclic skeletons. The selenation of pharmaceutical molecules is a promising way to discover new drugs. Herein, we introduced an electrochemical oxidative radical cascade cyclization of olefinic amides and diselenides without transition-metal catalysts and external oxidants. Various olefinic amides and diselenides were compatible, generating the desired products, more than 40 examples, in up to 94% yield. This selenocyclization reaction provided a facile method to construct C-Se and C-O bonds in one step.

Automated summary

Organoselenium compounds are important in medicinal chemistry, materials chemistry, and biochemistry. The selenation of pharmaceutical molecules is a promising method for discovering new drugs. This study introduces an electrochemical oxidative radical cascade cyclization of olefinic amides and diselenides without the need for transition-metal catalysts and external oxidants, resulting in high yields of desired products.