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3,4-Dihalo-2(5H)-furanones: a novel oxidant for the Glaser coupling reaction

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Abstract

5-Alkoxy-3,4-dihalo-2(5H)-furanones could be used as a kind of novel oxidant in the Glaser coupling reaction. The screening of reaction conditions showed that both PdCl2(PPh3)2 and 3,4-dichloro-5-methoxy-2(5H)-furanone played crucial roles in the reaction. A possible reaction mechanism was proposed according to the reactivity of 3,4-dihalo-2(5H)-furanones. The new method easily allows the syntheses of alkyl and aryl substituted 1,3-diyne compounds. However, carbyne polymer was unexpectedly obtained when using trimethylsilyl acetylene as the substrate under the Glaser reaction condition.

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Acknowledgments

We are grateful to the National Natural Science Foundation of China (no. 20772035) and the Natural Science Foundation of Guangdong Province (no. 5300082) for financial support.

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Authors and Affiliations

  1. Department of Chemistry, School of Chemistry and Environment, South China Normal University, Guangzhou, 510006, People’s Republic of China

    Jian-Xiao Li, Hao-Ran Liang, Zhao-Yang Wang & Jian-Hua Fu

  2. College of Chemistry, Sichuan University, Chengdu, 610064, People’s Republic of China

    Hao-Ran Liang

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  1. Jian-Xiao Li
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  2. Hao-Ran Liang
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  3. Zhao-Yang Wang
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  4. Jian-Hua Fu
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Correspondence to Zhao-Yang Wang.

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Li, JX., Liang, HR., Wang, ZY. et al. 3,4-Dihalo-2(5H)-furanones: a novel oxidant for the Glaser coupling reaction. Monatsh Chem 142, 507–513 (2011). https://doi.org/10.1007/s00706-011-0479-5

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  • DOI: https://doi.org/10.1007/s00706-011-0479-5

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