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Issue 6, 2019
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A metal-catalyzed new approach for α-alkynylation of cyclic amines

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Abstract

The first catalytic α-alkynylation of cyclic amines with the help of the N-propargylic group to afford 2-(1-alkynyl) N-allylic cyclic amines with an exclusive E-stereoselectivity for the in situ formed C[double bond, length as m-dash]C bond has been realized. Based on mechanistic studies, it is proven that the reaction proceeds through metal-mediated anti-1,5-hydride transfer forming an iminonium intermediate, which accepts the addition of the in situ generated 1-alkynyl metal species. The synthetic application has also been demonstrated.

Graphical abstract: A metal-catalyzed new approach for α-alkynylation of cyclic amines

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Publication details

The article was received on 16 Sep 2018, accepted on 24 Nov 2018 and first published on 26 Nov 2018


Article type: Edge Article
DOI: 10.1039/C8SC04115F
Chem. Sci., 2019,10, 1796-1801
  • Open access: Creative Commons BY license
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    A metal-catalyzed new approach for α-alkynylation of cyclic amines

    Y. Cui, W. Lin and S. Ma, Chem. Sci., 2019, 10, 1796
    DOI: 10.1039/C8SC04115F

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