Using fluoroform for constructing aromatic and heterocyclic trifluoromethylselenyl compounds

Abstract Fluoroform is used to prepare CuCF3 according to literature procedures. This nucleophilic trifluoromethyl moiety was reacted with aromatic and heterocyclic selenium cyanide derivatives to form the corresponding trifluoromethylselenium compounds. Selenium cyanides were made with 1,3-dicyanotriselenide prepared in situ from malononitrile and selenium dioxide. The electrophilicity of the reagent (δ+SeCN) was enough to attack aniline derivatives at the para position, but with other aromatics it was advantageous to use the corresponding boronic acid as the moiety was easily displaced by the selenium cyanate moiety.