86239-04-5Relevant academic research and scientific papers
Electrochemical-Promoted Nickel-Catalyzed Oxidative Fluoroalkylation of Aryl Iodides
Zou, Zhenlei,Li, Heyin,Huang, Mengjun,Zhang, Weigang,Zhi, Sanjun,Wang, Yi,Pan, Yi
supporting information, p. 8252 - 8256 (2021/11/01)
This work describes a general strategy for metal-catalyzed cross-coupling of fluoroalkyl radicals with aryl halides under electrochemical conditions. The contradiction between anodic oxidation of fluoroalkyl sulfinates and cathodic reduction of low-valent nickel catalysts can be well addressed by paired electrolysis, allowing for direct introduction of fluorinated functionalities into aromatic systems.
Organophotoredox Hydrodefluorination of Trifluoromethylarenes with Translational Applicability to Drug Discovery
Sap, Jeroen B.I.,Straathof, Natan J.W.,Knauber, Thomas,Meyer, Claudio F.,Meyer, Claudio F.,Médebielle, Maurice,Buglioni, Laura,Genicot, Christophe,Trabanco, Andrés A.,No?l, Timothy,Am Ende, Christopher W.,Gouverneur, Véronique
supporting information, p. 9181 - 9187 (2020/07/10)
Molecular editing such as insertion, deletion, and single atom exchange in highly functionalized compounds is an aspirational goal for all chemists. Here, we disclose a photoredox protocol for the replacement of a single fluorine atom with hydrogen in electron-deficient trifluoromethylarenes including complex drug molecules. A robustness screening experiment shows that this reductive defluorination tolerates a range of functional groups and heterocycles commonly found in bioactive molecules. Preliminary studies allude to a catalytic cycle whereby the excited state of the organophotocatalyst is reductively quenched by the hydrogen atom donor, and returned in its original oxidation state by the trifluoromethylarene.
Monofluoroalkyl-containing compound and its preparation method and use
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Paragraph 0066; 0067; 0068; 0069, (2017/07/31)
The invention discloses a monofluoroalkyl-containing compound and its preparation method. The preparation method comprises that in a solvent, in the presence of an alkali, an additive, a ligand and a catalyst, a compound A and a compound B undergo a suzuk
Facile Access to Fluoromethylated Arenes by Nickel-Catalyzed Cross-Coupling between Arylboronic Acids and Fluoromethyl Bromide
An, Lun,Xiao, Yu-Lan,Min, Qiao-Qiao,Zhang, Xingang
supporting information, p. 9079 - 9083 (2015/08/03)
The nickel-catalyzed fluoromethylation of arylboronic acids was achieved with the industrial raw material fluoromethyl bromide (CH2FBr) as the coupling partner. The reaction proceeded under mild reaction conditions with high efficiency; it features the use of a low-cost nickel catalyst, synthetic simplicity, and excellent functional-group compatibility, and provides facile access to fluoromethylated biologically relevant molecules. Preliminary mechanistic studies showed that a single-electron-transfer (SET) pathway is involved in the catalytic cycle.
Aromatic Retinoic Acid Analogues. 2. Synthesis and Pharmacological Activity
Dawson, Marcia I.,Chan, Rebecca,Hobbs, Peter D.,Chao, Wan-ru,Schiff, Leonard J.
, p. 1282 - 1293 (2007/10/02)
Aromatic analogues of (E)-1-(4-carboxyphenyl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)butadiene (1b) and its ethyl ester (1a) were synthesized as potential chemopreventive agents for the treatment of epithelial cancer and such skin diseases as psoriasis and cystic acne.The phenyl ring of 1 was replaced by 2-fluorophenyl, 2-methoxyphenyl, thienyl, furanyl, and pyridyl groups.The 1-fluorobutadiene analogue of 1 was also synthesized.With exception for the furanyl analogue, these compounds demonstrated good activity in reversing keratinization in hamster tracheal organ culture and in inhibiting the induction of ornithine decarboxylase in mouse epidermis by a tumor promoter.
