- Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis
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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.
- Webb, Eric W.,Park, John B.,Cole, Erin L.,Donnelly, David J.,Bonacorsi, Samuel J.,Ewing, William R.,Doyle, Abigail G.
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supporting information
p. 9493 - 9500
(2020/05/18)
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- Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex
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A metal- A nd photocatalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a single electron transfer (SET) event involving a photoexcited electron-donor-acceptor complex between an NHPI ester and a Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. The method provides an operationally simple, robust, and step-economical approach toward the construction of diversely functionalized dihydroquinolinones bearing quaternary centers. A sequential one-pot hydroalkylation-isomerization approach is also offered, giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance were observed in both approaches.
- Correia, José Tiago M.,Piva Da Silva, Gustavo,Kisukuri, Camila M.,André, Elias,Pires, Bruno,Carneiro, Pablo S.,Paixa?, Márcio W.
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p. 9820 - 9834
(2020/09/03)
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- ANTI-CANCER COMPOSITIONS AND METHODS OF USE
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This invention is directed to anticancer compounds, pharmaceutical compositions comprising the same, methods of making anticancer compounds, and methods of treating cancer with compounds and pharmaceutical compositions.
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Paragraph 00241; 00251; 00266; 00403; 00412; 00426; 00427
(2020/07/25)
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- Carboxylic acid derivative and application of carboxylic acid derivative serving as FXR (farnesoid X receptor) antagonist
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The invention relates to preparation of carboxylic acid derivatives and application of the carboxylic acid derivatives serving as an FXR (farnesoid X receptor) antagonist and particularly provides a compound shown as a formula (I), or a pharmaceutically a
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Paragraph 0040; 0041; 0042
(2017/08/28)
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- Novel derivative of 2-[3-cyano-4-isobutoxyphenyl]-4-methylthiazol-5-formic acid, preparation method for novel derivative and application of novel derivative
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The invention provides a compound as shown in a formula (I), or a pharmaceutical salt of the compound or stereisomers of the compound. The formula (I) is as shown in the specification. The compound as shown in the formula (I), or the pharmaceutical salt of the compound or the stereisomers of the compound applied to preventing and treating hyperuricemia have more superior uric-acid-reducing effect and more excellent safety compared to those of febuxostat.
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Paragraph 0083; 0107-0109
(2017/01/23)
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- LONG-ACTING CONTRACEPTIVE AGENTS: NORETHISTERONE ESTERS OF ARYLCARBOXYLIC ACIDS
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The synthesis of esters of norethisterone (17α-ethynyl-17β-hydroxyestr-4-en-3-one) with acids containing a benzene ring is described, two methods of esterification being compared in terms of yield and convenience.The activities of these esters as long-acting contraceptive agents have been evaluated.
- Wan, A. S. C.,Ngiam, T. L.,Leung, S. L.,Go, M. L.,Heng, P. W. S.,et al.
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p. 309 - 320
(2007/10/02)
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- Derivatives of benzoylphenoxyalkanoic acids having normolipemizing activity
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Derivatives of benzoylphenoxyalkanoic acids corresponding to the formula: STR1 wherein: X represents for example a halogen, R1 and R2 represent for example alkyl groups, R represents for example an aminoacid; and the salts thereof ar
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- Esters of 2-[4-(4-chlorobenzoyl)-phenoxy-2-methyl-propionic acid with bis-(hydroxyalkylthio)-alkanes
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Esters of 2-[4-(4-chlorobenzoyl)-phenoxy]-2-methylpropionic acid and bis-(hydroxyalkylthio)-alkanes of the formula: STR1 IN WHICH R is hydrogen or methyl are particularly useful in the prevention and treatment of hyperlipidaemia and hypercholesterolaemia.
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