3406-76-6Relevant articles and documents
Thioether compound, preparation method thereof, medical intermediate and application thereof
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Paragraph 0087-0094, (2020/08/27)
The invention relates to the technical field of chemical synthesis, and particularly discloses a thioether compound, a preparation method of the thioether compound, a medical intermediate and application of the medical intermediate, and the thioether compound is prepared from the following raw materials: a sulfoxide compound, a bromide and 1-butyl-3-methylimidazole trifluoromethanesulfonate. The thioether compound provided by the invention is reacted in ionic liquid 1-butyl-3-methylimidazole trifluoromethanesulfonate, a metal catalytic reaction is not needed, the problems of metal residues, organic solvent pollution and the like are fundamentally eliminated, and the thioether compound is particularly suitable for synthesis of some medicines and has relatively high economic applicability. The preparation method provided by the invention has the advantages of simple operation, high yield, high product purity, no need of metal catalysis in the whole reaction, mild reaction conditions andwide substrate range, solves the problem of easy generation of metal residues in the synthesized product due to use of transition metals for catalytic reaction in synthesis of thioether compounds in the prior art, and has a wide market prospect.
Sulfoxide Reduction/C(sp3)-S Metathesis Cascade in Ionic Liquid
Liu, Chenjing,Chen, Dengfeng,Fu, Yuanyuan,Wang, Fei,Luo, Jinyue,Huang, Shenlin
supporting information, p. 5701 - 5705 (2020/07/24)
A sulfoxide reduction/C-S bond metathesis cascade between sulfoxides and alkyl bromides has been developed to access high-value sulfides without the use of any catalysts or bases. In this cascade, classical Kornblum oxidation is employed to reduce sulfoxides with alkyl bromides in ionic liquid. This protocol features high functional tolerance, mild conditions, promising scalability, and sustainable solvents.
Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis
Webb, Eric W.,Park, John B.,Cole, Erin L.,Donnelly, David J.,Bonacorsi, Samuel J.,Ewing, William R.,Doyle, Abigail G.
supporting information, p. 9493 - 9500 (2020/05/18)
We report a redox-neutral method for nucleophilic fluorination of N-hydroxyphthalimide esters using an Ir photocatalyst under visible light irradiation. The method provides access to a broad range of aliphatic fluorides, including primary, secondary, and tertiary benzylic fluorides as well as unactivated tertiary fluorides, that are typically inaccessible by nucleophilic fluorination due to competing elimination. In addition, we show that the decarboxylative fluorination conditions are readily adapted to radiofluorination with [18F]KF. We propose that the reactions proceed by two electron transfers between the Ir catalyst and redox-active ester substrate to afford a carbocation intermediate that undergoes subsequent trapping by fluoride. Examples of trapping with O- and C-centered nucleophiles and deoxyfluorination via N-hydroxyphthalimidoyl oxalates are also presented, suggesting that this approach may offer a general blueprint for affecting redox-neutral SN1 substitutions under mild conditions.