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Computational insights into the mechanisms of Au(I)-catalysed intramolecular addition of the hydroxylamine group onto alkynes

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Abstract

Computational studies were carried out to understand the reaction mechanisms and the origin of the substrate-dependent chemo- and regio-selectivities of the Au(I)-catalysed intramolecular addition of the hydroxylamine group onto alkynes. For the terminal and the phenyl-substituted alkynes, the 5-exo O-attack and the 5-endo N-attack have been proposed and rationalized to be the most favorable pathway, respectively, in the initial cyclization step. In the case of terminal alkyne substrates, the proposed α-oxo gold carbenoid intermediate might not be a key intermediate in the subsequent formation of 3-pyrrolidinone.

Graphical abstract: Computational insights into the mechanisms of Au(i)-catalysed intramolecular addition of the hydroxylamine group onto alkynes

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Publication details

The article was received on 25 Jan 2017, accepted on 25 Feb 2017, published on 08 Mar 2017 and first published online on 08 Mar 2017


Article type: Research Article
DOI: 10.1039/C7QO00072C
Citation: Org. Chem. Front., 2017, Advance Article
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    Computational insights into the mechanisms of Au(I)-catalysed intramolecular addition of the hydroxylamine group onto alkynes

    H. Li, J. Liu, O. Abosede A. and X. Bao, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00072C

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