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Sila-spirocyclization involving unstrained C(sp3)−Si bond cleavage

Author

Listed:
  • Yufeng Shi

    (Nankai University)

  • Xiaonan Shi

    (Nankai University)

  • Jinyu Zhang

    (Nankai University)

  • Ying Qin

    (Nankai University)

  • Bo Li

    (California Institute of Technology)

  • Dongbing Zhao

    (Nankai University)

Abstract

C − Si Bond cleavage is one of the key elemental steps for a wide variety of silicon-based transformations. However, the cleavage of unstrained Si−C(sp3) bonds catalyzed by transition metal are still in their infancy. They generally involve the insertion of a M − C(sp2) species into the C − Si bond and consequent intramolecular C(sp2)‒Si coupling to exclusively produce siloles. Here we report the Pd-catalyzed sila-spirocyclization, in which the Si−C(sp3) bond is activated by the insertion of a M − C(sp3) species and followed by the formation of a new C(sp3)‒Si bond, allowing the construction of diverse spirosilacycles. This reactivity mode, which is strongly supported by DFT calculations may open an avenue for the Si−C(sp3) bond cleavage and silacycle synthesis.

Suggested Citation

  • Yufeng Shi & Xiaonan Shi & Jinyu Zhang & Ying Qin & Bo Li & Dongbing Zhao, 2022. "Sila-spirocyclization involving unstrained C(sp3)−Si bond cleavage," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-34466-4
    DOI: 10.1038/s41467-022-34466-4
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    References listed on IDEAS

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    1. Fei Ye & Yao Ge & Anke Spannenberg & Helfried Neumann & Matthias Beller, 2020. "The role of allyl ammonium salts in palladium-catalyzed cascade reactions towards the synthesis of spiro-fused heterocycles," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
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