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• W2950650797 endingPage "732" @default.
• W2950650797 startingPage "726" @default.
• W2950650797 abstract "A three-component reaction with lithiated alkoxyallenes, nitriles, and perfluorinated carboxylic acids as precursors led to a series of perfluoroalkyl- or perfluoroaryl-substituted 4-hydroxypyridine derivatives. These compounds were converted into 4-pyridyl nonaflates which can be employed as versatile building blocks for the synthesis of π-conjugated compounds with use of palladium-catalyzed couplings. Suzuki reactions at C-4 and C-3 of the pyridine ring proceeded with moderate to high yields. In addition, Suzuki−Miyaura, Stille, or Buchwald−Hartwig coupling reactions have also been studied and afforded the corresponding highly substituted pyridine derivatives. Starting from an arylated propargylic ether the three-component reaction led to a pentasubstituted 4-hydroxypyridine derivative that could also be employed in palladium-catalyzed processes at C-4 and at C-3 of the pyridine core. With this simple approach the sterically highly crowded 3,4,5-triphenyl-substituted pyridine derivative 37a could be prepared and studied by an X-ray analysis. With acetonitrile as precursor a different reaction pathway was found when this component was used in excess resulting in a pyridine derivative with a new substitution pattern. In summary, the methods described here allow a flexible and fairly efficient entry to a variety of highly substituted pyridine derivatives bearing perfluorinated alkyl or aryl groups." @default.
• W2950650797 created "2019-06-27" @default.
• W2950650797 creator A5025861277 @default.
• W2950650797 creator A5043767986 @default.
• W2950650797 creator A5060787706 @default.
• W2950650797 creator A5072825622 @default.
• W2950650797 creator A5081413658 @default.
• W2950650797 date "2009-12-23" @default.
• W2950650797 modified "2023-10-17" @default.
• W2950650797 title "Three-Component Synthesis of Perfluoroalkyl- or Perfluoroaryl-Substituted 4-Hydroxypyridine Derivatives and Their Palladium-Catalyzed Coupling Reactions" @default.
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• W2950650797 doi "https://doi.org/10.1021/jo9022183" @default.
• W2950650797 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/20030386" @default.
• W2950650797 hasPublicationYear "2009" @default.
• W2950650797 type Work @default.

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