Platinum Iodide-Catalyzed Three-Component Cascade Cycloaddition Reactions between γ-Aminoalkynes and Electron-Deficient Alkynes.

J Org Chem

The State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China.

Published: December 2021

Herein, we report a protocol for PtI-catalyzed three-component cascade cycloaddition reactions between γ-aminoalkynes and electron-deficient alkynes to afford highly substituted cyclohexadiene--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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http://dx.doi.org/10.1021/acs.joc.1c01913DOI Listing

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