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Radical-mediated C-C cleavage of unstrained cycloketones and DFT study for unusual regioselectivity

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  • Mingyang Wang

    (Soochow University)

  • Man Li

    (Nankai University)

  • Shan Yang

    (Soochow University)

  • Xiao-Song Xue

    (Nankai University)

  • Xinxin Wu

    (Soochow University)

  • Chen Zhu

    (Soochow University)

Abstract

The C-C σ-bond activation of unstrained cycloketones represents an ingenious and advanced technique in synthetic chemistry, but it remains a challenging area which has been largely underexplored. Herein we report an efficient strategy for the direct C-C cleavage of cyclohexanones and cyclopentanones. The cyclic C-C σ-bond is readily cleaved under mild conditions with the aid of an in situ formed side-chain aryl radical. Density functional theory calculations are carried out to shed light on the unusual regioselectivity of C-C bond cleavage. The reaction affords a variety of structurally diverse 3-coumaranones and indanones that widely exist in natural products and bioactive molecules, illustrating the synthetic value of this method.

Suggested Citation

  • Mingyang Wang & Man Li & Shan Yang & Xiao-Song Xue & Xinxin Wu & Chen Zhu, 2020. "Radical-mediated C-C cleavage of unstrained cycloketones and DFT study for unusual regioselectivity," Nature Communications, Nature, vol. 11(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-14435-5
    DOI: 10.1038/s41467-020-14435-5
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