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

Authors :
Tianlong Zeng
Xinhong Li
Jing Li
Chunhui Jiang
Jie Ren
Xiufang Xu
Lingyan Liu
Xiao Wang
Source :
The Journal of Organic Chemistry. 86:16614-16624
Publication Year :
2021
Publisher :
American Chemical Society (ACS), 2021.

Abstract

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.

Details

ISSN :
15206904 and 00223263
Volume :
86
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi...........2068df6702dc2b99d4bd931292c3e4b8