15875-69-1

Upstream product

• 3058-39-7 4-iodobenzonitrile 
• 1531595-91-1 [(2,2'-bipyridine)Cu(trifluoromethylselenolate)]₂ 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 75264-92-5 tetramethylammonium trifluoromethylselenate⁽⁰⁾ 
• 94706-45-3 4-Selenocyanato-benzonitrile 
• 873-74-5 4-Aminobenzonitrile 
• 623-03-0 4-Cyanochlorobenzene 
• 126747-14-6 4-cyanophenylboronic acid 

Downstream Products

• 15875-70-4 <4-Carboxy-phenyl>-trifluormethyl-selenid 

Relevant academic research and scientific papers

Copper-Catalyzed Direct Trifluoro- and Perfluoroalkylselenolations of Boronic Acids with a Shelf-Stable Family of Reagents

Herein the copper-catalyzed direct perfluoroalkylselenolation of aryl- and vinylboronic acids is described for the first time. The key to success is the design of new shelf-stable perfluoroalkylselenolating reagents, namely perfluoroalkyl tolueneselenosulfonates. The reaction occurs at room temperature in the presence of commercially available catalyst and ligand in catalytic quantities. (Figure presented.).

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.

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.

Trifluoromethylselenolation of Aryldiazonium Salts: A Mild and Convenient Copper-Catalyzed Procedure for the Introduction of the SeCF3 Group

The straightforward introduction of the trifluoromethylseleno group into aromatic and heteroaromatic compounds is accomplished by the utilization of readily available aryldiazonium tetrafluoroborates, potassium selenocyanate, and Ruppert-Prakash reagent. The reaction tolerates a wide range of aromatic and heteroaromatic diazonium salts and is also amenable to the synthesis of pentafluoroethyl selenoethers. Furthermore, the methodology can be applied directly starting from anilines.

Highly Efficient C-SeCF3 Coupling of Aryl Iodides Enabled by an Air-Stable Dinuclear PdI Catalyst

Building on our recent disclosure of catalysis at dinuclear PdI sites, we herein report the application of this concept to the realization of the first catalytic method to convert aryl iodides into the corresponding ArSeCF3 compounds. Highly efficient C-SeCF3 coupling of a range of aryl iodides was achieved, enabled by an air-, moisture-, and thermally stable dinuclear PdI catalyst. The novel SeCF3-bridged dinuclear PdI complex 3 was isolated, studied for its catalytic competence and shown to be recoverable. Experimental and computational data are presented in support of dinuclear PdI catalysis.

Copper-catalyzed trifluoromethylselenolation of aryl and alkyl halides: The silver effect in transmetalation

A catalytic trifluoromethylselenolation of aryl and alkyl halides by a Cu(I) catalyst has been developed. A key intermediate, [(phen)Cu(SeCF3)]2 (5) was successfully isolated and characterized by X-ray diffraction. The important role of silver in the tran

Synthesis of CuI trifluoromethylselenates for trifluoromethylselenolation of aryl and alkyl halides

The development of new strategies for synthesis of trifluoromethylthiolate compounds is of considerable importance in pharmaceuticals, agrochemicals, and advanced materials. Accordingly, currently much attention is being devoted to the development of effective methods and reagents for their synthesis. In contrast, considerably less effort has been afforded to the development of preparing C-SeCF3 bonds. Herein we report a concise route to synthesize a family of copper(I) trifluoromethylselenolate reagents by the reaction of CuI with the Ruppert's reagent (Me3SiCF3), KF, and elemental selenium in the presence of dinitrogen ligands in CH 3CN at room temperature. The reagent [Cu(bpy)(SeCF3)] 2 was proven to be air-stable and highly efficient for nucleophilic trifluoromethylthselenolation of a broad range of (hetero)aryl halides and alkyl halides. This method represents a powerful protocol for the construction trifluoromethylselenolate compounds. Copyright