17047-34-6Relevant academic research and scientific papers
Copper catalyzed oxidative coupling reactions for trifluoromethylselenolations-synthesis of R-SeCF3 compounds using air stable tetramethylammonium trifluoromethylselenate
Lefebvre, Quentin,Pluta, Roman,Rueping, Magnus
, p. 4394 - 4397 (2015)
The aerobic, room-temperature coupling of tetramethylammonium trifluoromethylselenate with readily available boronic acids, boronic esters, and terminal alkynes has been developed. The method permits direct access to valuable trifluoromethylselenoarenes and alkynes under mild conditions. A convenient one-pot reaction, a scale up procedure as well as an extension to perfluoroalkylselenates are also presented to further demonstrate the synthetic utility of this reaction.
Visible-Light-Mediated Metal-Free Synthesis of Trifluoromethylselenolated Arenes
Ghiazza, Clément,Debrauwer, Vincent,Monnereau, Cyrille,Khrouz, Lhoussain,Médebielle, Maurice,Billard, Thierry,Tlili, Anis
, p. 11781 - 11785 (2018/09/10)
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.
Divergent Reactivity of a Dinuclear (NHC)Nickel(I) Catalyst versus Nickel(0) Enables Chemoselective Trifluoromethylselenolation
Dürr, Alexander B.,Fisher, Henry C.,Kalvet, Indrek,Truong, Khai-Nghi,Schoenebeck, Franziska
supporting information, p. 13431 - 13435 (2017/10/17)
We herein showcase the ability of NHC-coordinated dinuclear NiI–NiI complexes to override fundamental reactivity limits of mononuclear (NHC)Ni0 catalysts in cross-couplings. This is demonstrated with the development of a chemoselective trifluoromethylselenolation of aryl iodides catalyzed by a NiI dimer. A novel SeCF3-bridged NiI dimer was isolated and shown to selectively react with Ar?I bonds. Our computational and experimental reactivity data suggest dinuclear NiI catalysis to be operative. The corresponding Ni0 species, on the other hand, suffers from preferred reaction with the product, ArSeCF3, over productive cross-coupling and is hence inactive.
Highly Efficient C-SeCF3 Coupling of Aryl Iodides Enabled by an Air-Stable Dinuclear PdI Catalyst
Aufiero, Marialuisa,Sperger, Theresa,Tsang, Althea S.-K.,Schoenebeck, Franziska
supporting information, p. 10322 - 10326 (2015/09/01)
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
Chen, Chaohuang,Hou, Chuanqi,Wang, Yuguang,Hor, T. S. Andy,Weng, Zhiqiang
supporting information, p. 524 - 527 (2014/04/03)
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
Chen, Chaohuang,Ouyang, Li,Lin, Quanfu,Liu, Yanpin,Hou, Chuanqi,Yuan, Yaofeng,Weng, Zhiqiang
supporting information, p. 657 - 661 (2014/01/23)
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
