Li Xinhong, Jiang Chunhui, Wang Xiao, Ren Jie, Zeng Tianlong, Xu Xiufang, Li Jing, Liu Lingyan
The State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China.
The College of Chemistry, Nankai University, Weijin Road 94#, Nankai District, Tianjin 300071, P. R. China.
J Org Chem. 2021 Dec 3;86(23):16614-16624. doi: 10.1021/acs.joc.1c01913. Epub 2021 Nov 9.
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.