Synthesis of 1,2-diselenides via potassium persulfate-mediated diselenation of allenamides with diselenides

An efficient potassium persulfate-mediated radical addition of allenamides with diselenides was developed to create a workable route to 1,2-diselenide products. The reaction tolerates a wide spectrum of functional groups to deliver the products in good to excellent yields. Mechanistic investigations including a calculation study indicated that the radical cascade proceeds through a vinyl radical intermediate, which is formed via a selenium radical added to the terminal C = C double bond of allenamides.

Automated summary

An efficient potassium persulfate-mediated radical addition of allenamides with diselenides was developed for the synthesis of 1,2-diselenide products. The reaction shows good tolerance towards a wide range of functional groups and delivers the products in good to excellent yields. Mechanistic investigations suggest that the reaction proceeds through a radical cascade involving a vinyl radical intermediate.