Cycloisomerization of Acetylenic Acids to γ‑Alkylidene Lactones using a Palladium(II) Catalyst Supported on Amino-Functionalized Siliceous Mesocellular Foam
Cycloisomerization of various γ-acetylenic acids to their corresponding γ-alkylidene lactones by the use of a heterogeneous Pd(II) catalyst supported on amino-functionalized siliceous mesocellular foam is described. Substrates containing terminal as well as internal alkynes were cyclized in high to...
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Veröffentlicht in: | Journal of organic chemistry 2014-02, Vol.79 (3), p.1399-1405 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Cycloisomerization of various γ-acetylenic acids to their corresponding γ-alkylidene lactones by the use of a heterogeneous Pd(II) catalyst supported on amino-functionalized siliceous mesocellular foam is described. Substrates containing terminal as well as internal alkynes were cyclized in high to excellent yields within 2–24 h under mild reaction conditions. The protocol exhibited high regio- and stereoselectivity, favoring the exo-dig product with high Z selectivity. Moreover, the catalyst displayed excellent stability under the employed reaction conditions, as demonstrated by its good recyclability and low leaching. |
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ISSN: | 0022-3263 1520-6904 1520-6904 |
DOI: | 10.1021/jo4028006 |