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Palladium-catalysed formation of vicinal all-carbon quaternary centres via propargylation

Author

Listed:
  • Xin Huang

    (Laboratory of Molecular Recognition and Synthesis, Zhejiang University)

  • Shangze Wu

    (Laboratory of Molecular Recognition and Synthesis, Zhejiang University)

  • Wangteng Wu

    (Laboratory of Molecular Recognition and Synthesis, Zhejiang University)

  • Pengbin Li

    (Laboratory of Molecular Recognition and Synthesis, Zhejiang University)

  • Chunling Fu

    (Laboratory of Molecular Recognition and Synthesis, Zhejiang University)

  • Shengming Ma

    (Laboratory of Molecular Recognition and Synthesis, Zhejiang University)

Abstract

Construction of two vicinal all-carbon quaternary carbon centres is of great importance due to the common presence of such units in natural and unnatural molecules with attractive functions. However, it remains a significant challenge. Here, we have developed a palladium-catalysed general coupling for the efficient connection of two tertiary carbon atoms: Specifically, propargylic carbonate has been treated with a fully loaded soft functionalized nucleophile to connect such two fully loaded carbon atoms with a simple palladium catalyst. It is observed that the central chirality in the optically active tertiary propargylic carbonates has been remembered and transferred into the products with very high efficiency. The triple bond and the functional groups such as ester, cyano and unsaturated C–C bonds make this method a relatively general solution for such a purpose due to their high synthetic versatility.

Suggested Citation

  • Xin Huang & Shangze Wu & Wangteng Wu & Pengbin Li & Chunling Fu & Shengming Ma, 2016. "Palladium-catalysed formation of vicinal all-carbon quaternary centres via propargylation," Nature Communications, Nature, vol. 7(1), pages 1-8, November.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms12382
    DOI: 10.1038/ncomms12382
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