- Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion
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We herein report a new catalytic method for intermolecular olefin aminofluorination using earth-abundant iron catalysts and nucleophilic fluoride ion. This method tolerates a broad range of unfunctionalized olefins, especially nonstyrenyl olefins that are incompatible with existing olefin aminofluorination methods. This new iron-catalyzed process directly converts readily available olefins to internal vicinal fluoro carbamates with high regioselectivity (N vs F), many of which are difficult to prepare using known methods. Preliminary mechanistic studies demonstrate that it is possible to exert asymmetric induction using chiral iron catalysts and that both an iron-nitrenoid and carbocation species may be reactive intermediates.
- Lu, Deng-Fu,Zhu, Cheng-Liang,Sears, Jeffrey D.,Xu, Hao
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supporting information
p. 11360 - 11367
(2016/10/12)
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- Fluorinated cannabinoid CB2 receptor ligands: Synthesis and in vitro binding characteristics of 2-oxoquinoline derivatives
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Cannabinoid receptor 2 (CB2) plays an important role in human physiology and the pathophysiology of different diseases, including neuroinflammation, neurodegeneration, and cancer. Several classes of CB2 receptor ligands, including 2-oxoquinoline derivatives, have been previously reported. We report the synthesis and results of in vitro receptor binding of a focused library of new fluorinated 2-oxoquinoline CB2 ligands. Twelve compounds, 13-16 18, 19, 21-24, 27, and 28 were synthesized in good yields in multiple steps. Human U87 glioma cells expressing either hCB1 (control) or hCB2 were generated via lentiviral transduction. In vitro competitive binding assay was performed using [3H]CP-55,940 in U87hCB1 and U87hCB2 cells. Inhibition constant (Ki) values of compounds 13-16, 18, 19, 21-24, 27, and 28 for CB2 were >10,000, 2.8, 5.0, 2.4, 22, 0.8, 1.4, >10,000, 486, 58, 620, and 2400 nM, respectively, and those for CB1 were >10,000 nM. Preliminary in vitro results suggest that six of these compounds may be useful for therapy of neuropathic pain, neuroinflammatory diseases and immune disorders. In addition, compound 19, with its subnanomolar Ki value, could be radiolabeled with 18F and explored for PET imaging of CB2 expression.
- Turkman, Nashaat,Shavrin, Aleksander,Ivanov, Roman A.,Rabinovich, Brian,Volgin, Andrei,Gelovani, Juri G.,Alauddin, Mian M.
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experimental part
p. 5698 - 5707
(2011/10/13)
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- SELECTIVE REDUCTION OF β-FLUOROAZIDES TO β-FLUOROAMINES
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Three methods were tested to reduce chemoselectively β-fluoroazides into β-fluoroamines : catalytic hydrogenation, catalytic transfer hydrogenation, and reduction with triphenyl phosphine.The last was the best.
- Hamman, S.,Beguin, C.G.
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p. 191 - 196
(2007/10/02)
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- Preparation of Fluoro Amines by the Reaction of Aziridines with Hydrogen Fluoride in Pyridine Solution
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Hydrogen fluoride combines regiospecifically with aziridines (1) to give 2-fluoro amines (6) in good yields.Fluorine attack is in all cases completely directed to the most substituted ring carbon or to the benzylic carbon.The results, for benzylic aziridi
- Wade, Tamsir N.
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p. 5328 - 5333
(2007/10/02)
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