290820-36-9Relevant academic research and scientific papers
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.
, p. 126 - 129 (2017)
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.
Pd0-mediated rapid C-[18F]fluoromethylation by the cross-coupling reaction of a [18f]fluoromethyl halide with an arylboronic acid ester: Novel method for the synthesis of a 18f- labeled molecular probe for positron emission tomography
Doi, Hisashi,Goto, Miki,Suzuki, Masaaki
, p. 1233 - 1238 (2012)
Pd0-Mediated C-[18F]fluoromethylation of pinacolborane-substituted benzoate 1 and [18F]FCH2X (X = Br or I) has been carried out with a focus on the rapid incorporation of a [18F]fluoromethyl group into an aryl carbon framework. The reaction of 1 and [18F]FCH2I under the conditions of [Pd 2(dba)3]/P(o-CH3C6H5)3 (1:6) and K2CO3 in DMF at 65 °C for 5min afforded the [18F]fluoromethylated benzoate [18F]-2 in 23% HPLC analytical yield. The coupling efficiency was significantly enhanced by the reaction of 1 and [18F]FCH2Br under the conditions of [Pd2(dba)3]/P(o-tolyl)3 (1:6) and K2CO3 in DMPU:H 2O (9:1) at 120 °C within 15min to afford [18F]-2 in 64% HPLC analytical yield (up to 86% HPLC analytical yield when strictly controlling the reaction temperature with ±3 °C accuracy) and 66% decay-corrected isolated yield based on [18F]FCH2Br. The total synthesis time starting from the production of 18F- in the cyclotron was 88min. The reaction was extended to various aryl compounds.
METHOD FOR HIGH-SPEED FLUOROMETHYLATION AND PROCESS FOR PREPARATION OF PET TRACER USING SAME
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Page/Page column 10-11, (2012/10/18)
Provided are: a method for rapid fluoromethylation, by which a fluoromethyl group can be easily bonded to an aromatic-ring carbon of an aromatic compound with little generation of by-products; and a process for preparation of a PET tracer using the same. The method is characterized by cross-coupling an organoboron compound in which an aromatic ring is bonded to a boron atom with FCX2Br (wherein X is ordinary hydrogen or heavy hydrogen) in a solvent obtained by adding water to an aprotic polar solvent, in the presence of a palladium complex, a phosphine ligand, and a base.
