78195-98-9Relevant academic research and scientific papers
Terminal Trifluoromethylation of Ketones via Selective C-C Cleavage of Cycloalkanols Enabled by Hypervalent Iodine Reagents
Wu, Shuang,Li, Junzhao,He, Ru,Jia, Kunfang,Chen, Yiyun
supporting information, p. 9204 - 9209 (2021/11/30)
We report the first terminal trifluoromethylation at aryl and alkyl ketones' ?, or more remote sites via the selective C-C bond cleavage of cycloalkanols. The noncovalent interactions between alcohols and hypervalent iodines(III) reagents were disclosed to activate both alcohols and the Togni I reagent in the dual photoredox/copper catalysis for the transformation. This reaction was scalable to the gram-scale synthesis, applicable to the structurally complex steroid trifluoromethylation, and extendable to the pentafluoroethylation.
Synthesis method of 4-cyclopentyl biphenyl fluorinated compound
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Paragraph 0018-0021; 0027; 0033, (2018/07/15)
The invention provides a synthesis method of a 4-cyclopentyl biphenyl fluorinated compound. The method comprises the steps of taking p-chloro-halobenzene as a starting material and carrying out Grignard reaction to generate a Grignard reagent II of the p-chloro-halogenated benzene; enabling the generated Grignard reagent II of the p-chloro-halogenated benzene and cyclopentanone to be subjected toa coupling reaction to generate cyclopentanol chlorobenzene; carrying out a dehydration reaction to generate cyclopentene chlorobenzene; carrying out a one-pot reaction to generate 4-cyclopentenyl phenylboronic acid; enabling the generated 4-cyclopentenyl phenylboronic acid and fluorinated halogenated benzene to be subjected to a coupling reaction to generate a 4-cyclopentenyl biphenyl fluorinatedcompound; carrying out a hydrogenation reaction to obtain the 4-cyclopentyl biphenyl fluorinated compound. The synthesis method provided by the invention has the characteristics of being high in conversion rate, low in cost, safe and stable in process, short in reaction steps, environmentally friendly in process route, and less in pollutant emission.
A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl–Alkyl Cross-Coupling Reactions
Greb, Andreas,Poh, Jian-Siang,Greed, Stephanie,Battilocchio, Claudio,Pasau, Patrick,Blakemore, David C.,Ley, Steven V.
supporting information, p. 16602 - 16605 (2017/12/13)
Coupling of readily available boronic acids and diazo compounds has emerged recently as a powerful metal-free carbon–carbon bond forming method. However, the difficulty in forming the unstable diazo compound partner in a mild fashion has hitherto limited their general use and the scope of the transformation. Here, we report the application of oxadiazolines as precursors for the generation of an unstable family of diazo compounds using flow UV photolysis and their first use in divergent protodeboronative and oxidative C(sp2)?C(sp3) cross-coupling processes, with excellent functional-group tolerance.
Regio- and enantioselective Baeyer-Villiger oxidation: Kinetic resolution of racemic 2-substituted cyclopentanones
Zhou, Lin,Liu, Xiaohua,Ji, Jie,Zhang, Yuheng,Wu, Wangbin,Liu, Yangbin,Lin, Lili,Feng, Xiaoming
supporting information, p. 3938 - 3941 (2014/08/18)
A kinetic resolution of racemic 2-substituted cyclopentanones via highly regio- and enantioselective Baeyer-Villiger oxidation has been successfully developed. The reaction could afford the normal 6-substituted δ-lactones in up to 98% ee and >19/1 regioselectivity. Meanwhile, the unreacted ketones were recovered in excellent ee values (up to 98%). It represents the best results of the kinetic resolution of racemic 2-substituted cyclopentanones via nonenzymic asymmetric BV oxidation.
