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Cadmium iodide-mediated allenylation of terminal alkynes with ketones

Author

Listed:
  • Xinjun Tang

    (State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences)

  • Can Zhu

    (State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences)

  • Tao Cao

    (State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences)

  • Jingqiang Kuang

    (State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences)

  • Weilong Lin

    (State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences)

  • Shengjun Ni

    (State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences)

  • Jiasheng Zhang

    (State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences)

  • Shengming Ma

    (State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
    Shanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University)

Abstract

Allenes are important building blocks in organic synthesis and have attracted much attention from researchers worldwide. So far, mono- and 1,3-disubstituted allenes can be prepared easily by applying the allenylation of terminal alkynes reaction of aldehydes. However, trisubstituted allenes have never been reported using this reaction due to the extremely low reactivity of ketones. Here, we report the one-pot synthesis of trisubstituted allenes from terminal alkynes and ketones utilizing cadmium iodide as the mediator. With this protocol, a series of different allenes, including 1,5-bisallenes and optically active allenols, which are especially important in synthetic chemistry, have been successfully prepared.

Suggested Citation

  • Xinjun Tang & Can Zhu & Tao Cao & Jingqiang Kuang & Weilong Lin & Shengjun Ni & Jiasheng Zhang & Shengming Ma, 2013. "Cadmium iodide-mediated allenylation of terminal alkynes with ketones," Nature Communications, Nature, vol. 4(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:4:y:2013:i:1:d:10.1038_ncomms3450
    DOI: 10.1038/ncomms3450
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