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Issue 17, 2019
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The mechanism of the gold-catalyzed intramolecular [3 + 2]-cycloaddition of 1,6-diynes: a DFT study

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Abstract

The gold-catalyzed [3 + 2] cycloaddition of areneyne-yne functionalities represents one of the most efficient methodologies for the construction of tricyclic ring systems under mild conditions. In the current report, a detailed mechanistic understanding of the reaction was achieved by DFT calculations. It was found that under the catalysis of gold(I), the initial cyclization occurs more favorably between the two alkynyl moieties via the 6-exo-dig pathway other than the arene-yne addition, which is the selectivity-determining step of the whole reaction and leads eventually to the [3 + 2] cycloadduct irreversibly by following the steps of arene-cation cyclization and proton transfer. Electronic and geometric factors are analyzed to better understand the calculation results.

Graphical abstract: The mechanism of the gold-catalyzed intramolecular [3 + 2]-cycloaddition of 1,6-diynes: a DFT study

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Publication details

The article was received on 04 Feb 2019, accepted on 25 Mar 2019 and first published on 25 Mar 2019


Article type: Paper
DOI: 10.1039/C9DT00553F
Citation: Dalton Trans., 2019,48, 5698-5704

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    The mechanism of the gold-catalyzed intramolecular [3 + 2]-cycloaddition of 1,6-diynes: a DFT study

    Y. Lin, T. Zhou, W. Guo, Z. Teng and Y. Xia, Dalton Trans., 2019, 48, 5698
    DOI: 10.1039/C9DT00553F

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