Photocatalytic Monofluorination of Unactivated C(sp3)–H Bonds by N-Fluorobenzenesulfimide Involving the Decatungstate Anion and the Effect of Water Additives on These Reactions
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The feasibility of efficient photocatalytic monofluorination of unactivated C(sp3)–H bonds of aliphatic amines, ketones, and alcohols in the presence of decatungstate anion and N-fluorobenzenesulfimide has been demonstrated. The presence of water facilitates not only a greater yield of the corresponding fluorine derivatives but also may affect the selectivity of these reactions. Cyclic voltammetry was used to show that one of the factors accounting for the promoting effect of water is an increase in the absolute values of the redox potentials for the oxidation of two- and one-electron-reduced forms of the decatungstate anion.
Key wordsphotoredox catalysis fluorination decatungstate anion
This work was carried out with the financial support of an Academy grant for Scientific Research of Young Scientists of the National Academy of Sciences of Ukraine during 2017-2018 (Contract No. 4M-18) and also partial financial support of the Targeted Joint Program for Research at the National Academy of Sciences of Ukraine on New Functional Substances and Materials for Chemical Production (Project No. 24).
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