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Unravelling the hidden link of lithium halides and application in the synthesis of organocuprates

Author

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  • Hong Yi

    (College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University)

  • Dali Yang

    (College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University)

  • Jie Xin

    (College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University)

  • Xiaotian Qi

    (School of Chemistry and Chemical Engineering, Chongqing University)

  • Yu Lan

    (School of Chemistry and Chemical Engineering, Chongqing University)

  • Yi Deng

    (College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University)

  • Chih-Wen Pao

    (National Synchrotron Radiation Research Center)

  • Jyh-Fu Lee

    (National Synchrotron Radiation Research Center)

  • Aiwen Lei

    (College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University
    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences)

Abstract

As a versatile metal, copper has demonstrated a wide application in acting as both organometallic reagent and catalyst. Organocuprates are among the most used organometallic reagents in the formation of new carbon–carbon bonds in organic synthesis. Therefore, revealing the real structures of organocuprates in solution is crucial to provide insights into the reactivity of organocuprates. Here we provide several important insights into organocuprate chemistry. The main finding contains the following aspects. The Cu(0) particles were detected via the reduction of CuX by nBuLi or PhLi. The Cu(II) precursors CuX2 (X=Cl, Br) could be used for the preparation of Gilman reagents. In addition, we provide direct evidence for the role and effect of LiX in organocuprate synthesis. Moreover, the EXAFS spectrum provides direct evidence for the exact structure of Li+ CuX2− ate complex in solution. This work not only sheds important light on the role of LiX in the formation of organocuprates but also reports two new routes for organocuprate synthesis.

Suggested Citation

  • Hong Yi & Dali Yang & Jie Xin & Xiaotian Qi & Yu Lan & Yi Deng & Chih-Wen Pao & Jyh-Fu Lee & Aiwen Lei, 2017. "Unravelling the hidden link of lithium halides and application in the synthesis of organocuprates," Nature Communications, Nature, vol. 8(1), pages 1-6, April.
    • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_ncomms14794
    DOI: 10.1038/ncomms14794
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    Cited by:

    1. Shunsuke Sasaki & Souvik Giri & Simon J. Cassidy & Sunita Dey & Maria Batuk & Daphne Vandemeulebroucke & Giannantonio Cibin & Ronald I. Smith & Philip Holdship & Clare P. Grey & Joke Hadermann & Simon, 2023. "Anion redox as a means to derive layered manganese oxychalcogenides with exotic intergrowth structures," Nature Communications, Nature, vol. 14(1), pages 1-11, December.

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