Nickel‐Catalyzed Electrochemical Synthesis of (Hetero)Aryl Trifluoromethyl Selenides

Serhii Krykun (1) , Muriel Durandetti (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

A convenient and efficient approach for the construction of aryl trifluoromethyl selenoethers from aryl iodides under mild conditions is reported. Electrochemical activation of stable and inexpensive NiBr2bipy (bipy – bipyridine) complex allows to avoid tedious Ni(COD)2 (COD – cyclooctadiene) catalyst. [NMe4][SeCF3] is employed as shelf-stable source of SeCF3 fragment and reaction is shown to tolerate wide range of substrates, including modification of drug-like molecules. Cyclic voltammetry studies allow insight into the reaction mechanism.

Keywords: C–Se bond formation ; Electrosynthesis ; Nickel catalysis ; Selenium ; Trifluoromethylselenolation

Domains: Chemical Sciences; Organic chemistry

Serhii Krykun, Muriel Durandetti. Nickel‐Catalyzed Electrochemical Synthesis of (Hetero)Aryl Trifluoromethyl Selenides. European Journal of Organic Chemistry, 2023, 26 (4), pp.e202201393. ⟨10.1002/ejoc.202201393⟩. ⟨hal-03955442⟩