Solvent‐Regulated Electrochemical Selenylation and Deuteration of Alkynyl Aryl Ketones: Chemoselective Synthesis of 3‐Selenylated Chromones and Deutero‐Selenylated Chalcones

Abstract

We have developed an electrochemical reaction for the synthesis of 3‐selenylchromones and deutero‐selenylated chalcones of alkynyl aryl ketones. This method is free from metal catalysts and oxidants, and is regulated by solvents. The reaction conditions are mild, and a wide range of substrates can be employed to produce selenylated chromones and deutero‐selenylated chalcones, displaying potential anti‐inflammatory activities. Furthermore, we have demonstrated the applicability of this approach for the late‐stage deutero‐selenylation of the drug molecule, metochalcone.

Ag(i)-catalyzed three-component radical cascade synthesis of 3-organoselenyl chromones from 2-methoxyaryl alkynones, Se powder and organic boronic acids

“…The first one is the electrophilic cascade cyclization of 2-methoxyaryl alkyones with organoselenium cations, which were in situ generated via oxidation of RSeSeR with various chemical oxidants, such as FeCl 3 , 4 PIFA, 5 Oxone 6 or Selectfluor. 7 Not long ago, the electrooxidation method was also explored by the Ruan group for the preparation of 3-organoselenyl chromones via this approach 8 (Scheme 1a). Considering that RSeSeR was not commercially available, Zhang and co-workers 9 also recently improved this approach by their pre-preparation from excessive organic boronic acids and Se powder, followed by oxidation with PIFA and cyclization in one pot.…”