Synthesis of Selenium Derivatives using Organic Selenocyanates as Masked Selenols: Chemical Reduction with Rongalite as a Simpler Tool to give Nucleophilic Selenides

Abstract

The chemical reduction within a family of organic selenocyanates, as masked selenols, using reducing agents, such as Rongalite, sodium dithionite, and sodium thiosulfate is investigated. Using Rongalite, the corresponding diselenides were obtained quantitatively and selectively in very good to excellentyields (51–100%) starting from alkyl, aryl, and benzyl selenocyanates. The scope of the reaction is unaffected by the electronic nature of the substituents. Furthermore, the reducing agent Rongalite, is compatible with hydrolysable and reducingsensitive functional groups. Additionally, a simple methodology employing the in-situ generated benzyl selenolate anion (PhCH2Se- ) to promote aliphatic nucleophilic substitution, epoxide ring opening, and Michael addition reactions has beendeveloped; thus, extending the structural diversity of the synthesized selenium derivatives.