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Issue 2, 2015
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Atom-economic generation of gold carbenes: gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles

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Abstract

The generation of gold carbenes via the gold-catalyzed intermolecular reaction of nucleophiles containing relatively labile N–O or N–N bonds with alkynes has received considerable attention during recent years. However, this protocol is not atom-economic as the reaction produces a stoichiometric amount of pyridine or quinoline waste, the cleaved part of the N–O or N–N bonds. In this article, we disclose an unprecedented gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles, allowing rapid and practical access to a wide range of synthetically-useful 2-aminopyrroles. Most importantly, mechanistic studies and theoretical calculations revealed that this reaction presumably proceeds via an α-imino gold carbene pathway, thus providing a strategically novel, atom-economic route to the generation of gold carbenes. Other significant features of this approach include the use of readily-available starting materials, high flexibility, simple procedure, mild reaction conditions, and in particular, no need to exclude moisture or air (“open flask”).

Graphical abstract: Atom-economic generation of gold carbenes: gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles

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Publication details

The article was received on 26 Aug 2014, accepted on 12 Nov 2014 and first published on 12 Nov 2014


Article type: Edge Article
DOI: 10.1039/C4SC02596B
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Chem. Sci., 2015,6, 1265-1271
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    Atom-economic generation of gold carbenes: gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles

    A. Zhou, Q. He, C. Shu, Y. Yu, S. Liu, T. Zhao, W. Zhang, X. Lu and L. Ye, Chem. Sci., 2015, 6, 1265
    DOI: 10.1039/C4SC02596B

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