64747-74-6Relevant academic research and scientific papers
Nickel-catalyzed monofluoromethylation of (hetero)aryl bromides via reductive cross-coupling
Yin, Han,Sheng, Jie,Zhang, Kai-Fan,Zhang, Zi-Qi,Bian, Kang-Jie,Wang, Xi-Sheng
supporting information, p. 7635 - 7638 (2019/07/09)
A mild and efficient nickel-catalyzed direct monofluoromethylation of (hetero)aryl bromides by reductive cross-coupling has been developed. This method exhibits good efficiency, wide functional-group compatibility, and suitability for aryl and heteroaryl bromides with abundant industrial raw material BrCH2F. This strategy provides an efficient way to synthesize monofluoromethylated molecules for drug discovery.
Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Monofluoroalkyl Halides for Late-Stage Monofluoroalkylation
Sheng, Jie,Ni, Hui-Qi,Zhang, Hao-Ran,Zhang, Kai-Fan,Wang, Yi-Ning,Wang, Xi-Sheng
supporting information, p. 7634 - 7639 (2018/06/26)
A combinatorial nickel-catalyzed monofluoroalkylation of aryl halides with unactivated fluoroalkyl halides by reductive cross-coupling has been developed. This method demonstrated high efficiency, mild conditions, and excellent functional-group tolerance, thus enabling the late-stage monofluoroalkylation of diverse drugs. The key to success was the combination of diverse readily available bidentate and monodentate pyridine-type nitrogen ligands with nickel, which in situ generated a variety of readily tunable catalysts to promote fluoroalkylation with broad scope with respect to both coupling partners. This combinatorial catalysis strategy offers a solution for nickel-catalyzed reductive cross-coupling reactions and provides an efficient way to synthesize fluoroalkylated druglike molecules for drug discovery.
Metal-free18F-labeling of aryl-CF2H via nucleophilic radiofluorination and oxidative C-H activation
Yuan, Gengyang,Wang, Feng,Stephenson, Nickeisha A.,Wang, Lu,Rotstein, Benjamin H.,Vasdev, Neil,Tang, Pingping,Liang, Steven H.
supporting information, p. 126 - 129 (2016/12/27)
A metal-free and selective method to form [18F]aryl-CF2H through nucleophilic radiofluorination of benzyl (pseudo)halides and oxidative C-H activation of benzylic C-H bonds has been developed. The method is operationally simple and tolerates a variety of electron-neutral/deficient arenes and heteroarenes.
Transition-metal-free C-H oxidative activation: Persulfate-promoted selective benzylic mono- and difluorination
Ma, Jing-Jing,Yi, Wen-Bin,Lu, Guo-Ping,Cai, Chun
supporting information, p. 2890 - 2894 (2015/04/27)
An operationally simple and selective method for the direct conversion of benzylic C-H to C-F to obtain mono- and difluoromethylated arenes using Selectfluor as a fluorine source is developed. Persulfate can be used to selectively activate benzylic hydrogen atoms toward C-F bond formation without the aid of transition metal catalysts.
Selective electrolytic fluorinations in 70% HF/30% pyridine
Lee, Sarah M.,Roseman, Jamie M.,Zartman, C. Blair,Morrison, Eamonn P.,Harrison, Sean J.,Stankiewicz, Corrie A.,Middleton
, p. 65 - 70 (2007/10/03)
The selective fluorination of compounds containing benzylic hydrogen atoms was accomplished by electrolysis in a mixture of 70% HF and 30% pyridine (Olah's reagent) using a square wave alternating current (1.76-2.75 V, 0.02-0.05 Hz) and Pt electrodes. This method can be used in the laboratory to prepare conveniently gram-size quantities of monofluorinated products. An ion radical mechanism has been proposed.
