Facile and General Electrochemical Diselenylation of Terminal Alkynes

Difunctionalization of terminal alkynes is a cutting-edge method for producing trisubstituted alkenes. The methods employed, however, rely heavily on the use of organometallic species with harsh conditions or transition metal-catalyzed multicomponent radical-mediated transformations. Herein, we report an electrochemical diselenylation of terminal alkynes to afford trisubstituted alkenes in an antiselective fashion with 100% atom economy. Moreover, this method uses simple graphite as electrodes and MeCN as a solvent and does not require high temperatures, which affords trisubstituted alkenes with high regioselectivity. The success of the gram-scale reaction, great tolerance to multiple functional groups, and the functionalization of complex compounds all established the value of this green technology.

Automated summary

This article reports an electrochemical diselenylation method for terminal alkynes, obtaining trisubstituted alkenes in an antiselective manner with 100% atom economy. This green technology uses simple graphite electrodes and MeCN as solvent, without requiring high temperatures, resulting in high regioselectivity for trisubstituted alkenes. The successful gram-scale reaction, tolerance to multiple functional groups, and functionalization of complex compounds highlight the importance of this method.