2777-66-4Relevant articles and documents
Synthesis of β-Fluorovinyliodonium Salts by the Reaction of Alkynes with Hypervalent Iodine/HF Reagents
Kitamura, Tsugio,Mizuno, Shota,Muta, Kensuke,Oyamada, Juzo
, p. 2773 - 2778 (2018)
The reaction of alkynes with PhIO and Py·HF followed by treatment with BF3·OEt2 gave β-fluorovinyliodonium tetrafluoroborates in good to high yields. More conveniently, the reaction using PhI and Py·HF in the presence of m-CPBA also afforded β-fluorovinyliodonium tetrafluoroborates in good yields. These methods have the advantages that β-fluorovinyliodonium salts can be prepared without ArIF2.
Nickel-Mediated Alkoxycarbonylation for Complete Carbon Isotope Replacement
Ton, Stephanie J.,Neumann, Karoline T.,N?rby, Peter,Skrydstrup, Troels
supporting information, p. 17816 - 17824 (2021/11/04)
Many commercial drugs, as well as upcoming pharmaceutically active compounds in the pipeline, display aliphatic carboxylic acids or derivatives thereof as key structural entities. Synthetic methods for rapidly accessing isotopologues of such compounds are highly relevant for undertaking critical pharmacological studies. In this paper, we disclose a direct synthetic route allowing for full carbon isotope replacement via a nickel-mediated alkoxycarbonylation. Employing a nickelII pincer complex ([(N2N)Ni-Cl]) in combination with carbon-13 labeled CO, alkyl iodide, sodium methoxide, photocatalyst, and blue LED light, it was possible to generate the corresponding isotopically labeled aliphatic carboxylates in good yields. Furthermore, the developed methodology was applied to the carbon isotope substitution of several pharmaceutically active compounds, whereby complete carbon-13 labeling was successfully accomplished. It was initially proposed that the carboxylation step would proceed via the in situ formation of a nickellacarboxylate, generated by CO insertion into the Ni-alkoxide bond. However, preliminary mechanistic investigations suggest an alternative pathway involving attack of an open shell species generated from the alkyl halide to a metal ligated CO to generate an acyl NiIII species. Subsequent reductive elimination involving the alkoxide eventually leads to carboxylate formation. An excess of the alkoxide was essential for obtaining a high yield of the product. In general, the presented methodology provides a simple and convenient setup for the synthesis and carbon isotope labeling of aliphatic carboxylates, while providing new insights about the reactivity of the N2N nickel pincer complex applied.
HYDROXY FATTY ACID COMPOUNDS AND USES THEREOF FOR DISEASE TREATMENT AND DIAGNOSIS
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, (2011/02/24)
A compound of formula (I): wherein R represents a hydroxy substituted C24 - C40 straight chain aliphatic group containing at least one double bond in the carbon chain; and at least one carbon in the chain is substituted with a hydroxy group. Such compounds are useful for detecting inflammation, inflammatory disorders and cancer in a subject, and can also be used in therapeutic applications including treatment and/or prevention of these conditions. Pharmaceutical compositions, combinations and supplements, as well as methods of treatment using the described compounds are therefore also described.
