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
Hauptverfasser: Li, Xinhong, Jiang, Chunhui, Wang, Xiao, Ren, Jie, Zeng, Tianlong, Xu, Xiufang, Li, Jing, Liu, Lingyan
Format: Artikel
Sprache:eng
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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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01913