One-pot four-component assembly for diselenocarbamates?

Organic Chemistry Frontiers Pub Date: 2021-10-15 DOI: 10.1039/D1QO01288F

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 [R2R3N[double bond, length as m-dash]CHCl]+Cl?, formed from chloroform and amine in the presence of a base, was captured by diselane via nucleophilic substitution to afford the intermediate [R2R3N[double bond, length as m-dash]CHSeR1]+Cl?. With the help of a base, the desired diselenocarbamate was successfully achieved through a carbene intermediate [(R2R3N)(SeR1)C:] with selenium powder.

Graphical abstract: One-pot four-component assembly for diselenocarbamates
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