Electrochemical oxidative selenocyclization of olefinic amides towards the synthesis of iminoisobenzofurans?

Organic Chemistry Frontiers Pub Date: 2022-04-08 DOI: 10.1039/D2QO00406B

Abstract

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.

Graphical abstract: Electrochemical oxidative selenocyclization of olefinic amides towards the synthesis of iminoisobenzofurans
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