5172-98-5

Upstream product

• 62-53-3 aniline 
• 10336-11-5 4-aminophenylselenocyanate 
• 75-46-7 trifluoromethan 
• 860001-89-4 acetic acid-(4-selenocyanato-anilide) 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 622-50-4 4-Acetamido-1-iodobenzene 
• 75264-92-5 tetramethylammonium trifluoromethylselenate⁽⁰⁾ 

Downstream Products

• 27143-00-6 N-(4-trifluoromethylselanyl-phenyl)-thioacetamide 

Relevant academic research and scientific papers

Using fluoroform for constructing aromatic and heterocyclic trifluoromethylselenyl compounds

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.

Visible-Light-Mediated Metal-Free Synthesis of Trifluoromethylselenolated Arenes

The first visible-light-mediated synthesis of trifluoromethylselenolated arenes under metal-free conditions is reported. The use of an organic photocatalyst enables the trifluoromethylselenolation of arene diazonium salts using the shelf-stable reagent trifluoromethyl tolueneselenosulfonate at room temperature. The reaction does not require the presence of any additives and shows high functional-group tolerance, covering a very broad range of starting materials. Mechanistic investigations, including EPR spectroscopy, luminescence investigations, and cyclic voltammetry allow rationalization of the reaction mechanism.

Nickel-Catalyzed Trifluoromethylselenolation of Aryl Halides Using the Readily Available [Me4N][SeCF3] Salt

A convenient and efficient method for the construction of aryl trifluoromethyl selenoethers from the corresponding aryl halides in the presence of Ni(COD)2 and an appropriate ligand is reported. Various aryl iodides, bromides, and chlorides were smoothly converted in this reaction by simply varying the ligand, which afforded aryl and heteroaryl trifluoromethyl selenoethers in good to almost quantitative yields. The reaction was also applicable to the synthesis of druglike molecules. This work is the first report for trifluoromethylselenolation of aryl chlorides. Advantages of the present Ni-catalyzed approach include mild reaction conditions, good functional group tolerance, inexpensive reagents, easy operation, and no use of additional additives. This protocol allows for a straightforward and reliable access to trifluoromethyl selenides that are latent screening candidates for new pharmaceuticals and agrochemicals.

Sandmeyer-Type Trifluoromethylthiolation and Trifluoromethylselenolation of (Hetero)Aromatic Amines Catalyzed by Copper

Aromatic and heteroaromatic diazonium salts were efficiently converted into the corresponding trifluoromethylthio- or selenoethers by reaction with Me4NSCF3 or Me4NSeCF3, respectively, in the presence of catalytic amounts of copper thiocyanate. These Sandmeyer-type reactions proceed within one hour at room temperature, are applicable to a wide range of functionalized molecules, and can optionally be combined with the diazotizations into one-pot protocols.