An electrocatalytic three-component cyclization reaction: synthesis of selenium-containing cyclopentenes via intermolecular selective [3 + 2] annulation of terminal alkynes, unsaturated propionates, and diselenides

Abstract

Developing efficient electrochemically mediated three component cyclization reactions involving diselenides is of great significance for constructing structurally diverse organoselenium compounds. Herein, a novel electrocatalytic three-component cyclization reaction of terminal alkynes, unsaturated propionates, and diselenides has been developed, providing a simple and effective method for the synthesis of valuable selenocyclopentenes. This strategy uses inexpensive ferrocene as a redox catalyst to obtain a series of selenium-containing cyclopentene derivatives in moderate to excellent yields, characterized by mild reaction conditions, a wide substrate range, and good functional group tolerance. Preliminary mechanistic studies have been conducted, indicating that selenium radicals, selenium anions, carbon radicals, and carbocations are involved in this transformation.