1333415-77-2Relevant academic research and scientific papers
Triphenylphosphine-Mediated Deoxygenative Reduction of CF3SO2Na and Its Application for Trifluoromethylthiolation of Aryl Iodides
Yang, Yi,Xu, Long,Yu, Siqi,Liu, Xiaoqiang,Zhang, Yu,Vicic, David A.
, p. 858 - 863 (2016)
We report herein a practical method for taming Langlois' reagent CF3SO2Na to generate CuSCF3 by a triphenylphospine-mediated deoxygenative reduction process. This chemistry highlights a novel utilization of the inherent CF3S skeleton of Langlois' reagent as a CF3S feedstock under mild conditions. The CuSCF3 intermediate generated by this protocol can react with a wide array of supporting ligands to furnish several air-stable [LCu(SCF3)] complexes as valuable trifluoromethylthiolating agents. In addition, the CuSCF3 intermediate can be directly employed for the trifluoromethylthiolation of (hetero)aryl iodides with operational simplicity and atomic efficiency. Efficient synthesis! A low cost method for the generation of CuSCF3 by a triphenylphospine-mediated deoxygenative reduction of Langlois' reagent (CF3SO2Na) has been developed (see scheme). This method can be applied for the convenient synthesis of a wide array of ligated and air-stable CuSCF3 complexes. Additionally, the CuSCF3 complexes generated in situ by this protocol were found to trifluoromethylthiolate (hetero)aryl iodides with high efficiency.
Metal-Free Trifluoromethylthiolation of Arylazo Sulfones
Li, Ankun,Li, Yuxuan,Liu, Junjie,Chen, Jingqi,Lu, Kui,Qiu, Di,Fagnoni, Maurizio,Protti, Stefano,Zhao, Xia
, p. 1292 - 1299 (2021)
A visible-light-driven protocol for the synthesis of aryl trifluoromethyl thioethers under photocatalyst- and metal-free conditions has been pursued. The procedure exploits the peculiar properties of arylazo sulfones (having electron-rich or electron-poor substituents on the (hetero)aromatic ring) as photochemical precursors of aryl radicals and S-trifluoromethyl arylsulfonothioates as easy-to-handle trifluoromethylthiolating agents.
Transition-Metal-Free ipso-Trifluoromethylthiolation of Lithium Aryl Boronates
Shen, Feng,Zheng, Hanliang,Xue, Xiao-Song,Lu, Long,Shen, Qilong
, p. 6347 - 6351 (2019/08/20)
A transition-metal-free direct trifluoromethylthiolation of the ipso-carbon of lithium aryl boronates with trifluoromethanesulfenate under mild conditions was described. In addition, late-stage site-selective C-H borylation/trifluoromethylation and C-Cl b
Synthesis and Reactivity of α-Cumyl Bromodifluoromethanesulfenate: Application to the Radiosynthesis of [18F]ArylSCF3
Wu, Jiang,Zhao, Qunchao,Wilson, Thomas C.,Verhoog, Stefan,Lu, Long,Gouverneur, Véronique,Shen, Qilong
supporting information, p. 2413 - 2417 (2019/02/01)
A highly reactive electrophilic bromodifluoromethylthiolating reagent, α-cumyl bromodifluoro-methanesulfenate 1, was prepared to allow for direct bromodifluoromethylthiolation of aryl boron reagents. This coupling reaction takes place under copper catalysis, and affords a large range of bromodifluoromethylthiolated arenes. These compounds are amenable to various transformations including halogen exchange with [18F]KF/K222, a process giving access to [18F]arylSCF3 in two steps from the corresponding aryl boronic pinacol esters.
Trifluoromethylthiolation of aryl iodides and bromides enabled by a bench-stable and easy-to-recover dinuclear palladium(I) catalyst
Yin, Guoyin,Kalvet, Indrek,Schoenebeck, Franziska
supporting information, p. 6809 - 6813 (2015/06/08)
Abstract While palladium catalysis is ubiquitous in modern chemical research, the recovery of the active transition-metal complex under routine laboratory applications is frequently challenging. Described herein is the concept of alternative cross-coupling cycles with a more robust (air-, moisture-, and thermally-stable) dinuclear PdI complex, thus avoiding the handling of sensitive Pd0 species or ligands. Highly efficient C-SCF3 coupling of a range of aryl iodides and bromides was achieved, and the recovery of the PdI complex was accomplished via simple open-atmosphere column chromatography. Kinetic and computational data support the feasibility of dinuclear PdI catalysis. A novel SCF3-bridged PdI dimer was isolated, characterized by X-ray crystallography, and verified to be a competent catalytic intermediate. Pd double team: The cross-coupling enabled by an air-, moisture-, and thermally stable dinuclear PdI complex was explored. Highly efficient C-SCF3 coupling of a range of aryl iodides and bromides was achieved and the catalyst was recovered by simple column chromatography, thus highlighting its robustness and the possibility for catalyst recycling. Kinetic and computational data support the feasibility of dinuclear PdI catalysis.
Nickel-catalyzed synthesis of aryl trifluoromethyl sulfides at room temperature
Zhang, Cheng-Pan,Vicic, David A.
supporting information; experimental part, p. 183 - 185 (2012/03/07)
Inexpensive nickel-bipyridine complexes were found to be active for the trifluoromethylthiolation of aryl iodides and aryl bromides at room temperature using the convenient [NMe4][SCF3] reagent.
Pd-catalyzed synthesis of Ar-SCF3 compounds under mild conditions
Teverovskiy, Georgiy,Surry, David S.,Buchwald, Stephen L.
supporting information; experimental part, p. 7312 - 7314 (2011/10/03)
Good to excellent yields of aryl trifluoromethyl sulfides, which are an important class of compounds in both the pharmaceutical and agrochemical areas, can be achieved under mild conditions by the Pd-catalyzed reaction of aryl bromides with a trifluoromethylthiolate nucleophile (see scheme). Copyright
