One-pot four-component assembly for diselenocarbamates

Abstract

A one-pot four-component synthesis of diselenocarbamates was established from the combination of diselanes, selenium powder, chloroform and amines under mild conditions. A total of 36 diselenocarbamates were achieved in a straightforward manner in up to 91% yield. The zwitterionic intermediate [R²R³NCHCl]⁺Cl⁻, formed from chloroform and amine in the presence of a base, was captured by diselane via nucleophilic substitution to afford the intermediate [R²R³NCHSeR¹]⁺Cl⁻. With the help of a base, the desired diselenocarbamate was successfully achieved through a carbene intermediate [(R²R³N)(SeR¹)C:] with selenium powder.