17047-34-6Relevant articles and documents
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.
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.
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