Platinum Iodide-Catalyzed Formal Three-Component Cascade Cycloaddition Reactions between γ‑Aminoalkynes and Electron-Deficient Alkynes
Herein, we report a protocol for PtI2-catalyzed formal three-component cascade cycloaddition reactions between γ-aminoalkynes and electron-deficient alkynes to afford highly substituted cyclohexadiene-b-pyrrolidines in good yields. On the basis of the results of the control experiments and density f...
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Veröffentlicht in: | Journal of organic chemistry 2021-12, Vol.86 (23), p.16614-16624 |
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Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | Herein, we report a protocol for PtI2-catalyzed formal three-component cascade cycloaddition reactions between γ-aminoalkynes and electron-deficient alkynes to afford highly substituted cyclohexadiene-b-pyrrolidines in good yields. On the basis of the results of the control experiments and density functional theory calculations, we present a plausible mechanism that proceeds via two key intermediates. The overall transformation involves the cleavage and formation of multiple C–C and C–N bonds and a previously unreported reaction mode of a seven-membered nitrogen heterocyclic intermediate. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.1c01913 |