Electron-Deficient Acetylenes as Three-Modal Adjuvants in S<sub>N</sub><sup>H</sup> Reaction of Pyridinoids with Phosphorus Nucleophiles
Publications covering a new easy metal-free functionalization of pyridinoids (pyridines, quinolines, isoquinolines, acridine) under the action of the system of electron-deficient acetylenes (acetylenecarboxylic acid esters, acylacetylenes)/<i>P</i>-nucleophiles (phosphine chalcogenides,...
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| Autores principales: | , , |
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| Formato: | article |
| Lenguaje: | EN |
| Publicado: |
MDPI AG
2021
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| Materias: | |
| Acceso en línea: | https://doaj.org/article/8dadd64bf56a46039b2a1f486fa621ae |
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| Sumario: | Publications covering a new easy metal-free functionalization of pyridinoids (pyridines, quinolines, isoquinolines, acridine) under the action of the system of electron-deficient acetylenes (acetylenecarboxylic acid esters, acylacetylenes)/<i>P</i>-nucleophiles (phosphine chalcogenides, <i>H</i>-phosphonates) are reviewed. Special attention is focused on a S<sub>N</sub><sup>H</sup> reaction of the regioselective cross-coupling of pyridines with secondary phosphine chalcogenides triggered by acylacetylenes to give 4-chalcogenophosphorylpyridines. In these processes, acetylenes act as three-modal adjuvants (i) activating the pyridine ring towards <i>P</i>-nucleophiles, (ii) deprotonating the P-H bond and (iii) facilitating the nucleophilic addition of the <i>P</i>-centered anion to a heterocyclic moiety followed by the release of the selectively reduced acetylenes (<i>E</i>-alkenes). |
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