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Nickel-catalyzed switchable 1,3-dienylation and enantioselective allenylation of phosphine oxides

Author

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  • Jiayin Zhang

    (University of Science and Technology of China)

  • Xihao Chang

    (University of Science and Technology of China)

  • Xianghong Xu

    (University of Science and Technology of China)

  • Hongyi Wang

    (University of Science and Technology of China)

  • Lingzi Peng

    (University of Science and Technology of China)

  • Chang Guo

    (University of Science and Technology of China)

Abstract

The development of general catalytic methods for the regio- and stereoselective construction of phosphoryl derivatives from identical substrates remains a formidable challenge in organic synthesis. Enabled by the newly developed BDPP-type ligands, we disclosed a nickel-catalyzed allenylation of phosphine oxides rationally and predictably, allowing the construction of versatile chiral allenylphosphoryl derivatives with high enantiopurity (up to 94% e.e.). Alternatively, using an achiral phosphine ligand dcypbz under acidic conditions, we achieved a regiochemical switch of the 1,3-dienylation to afford functionalized phosphinoyl 1,3-butadienes (up to 93% yield). The salient features of this method include switchable reactivity, broad substrate scope, readily available feedstock, single-step preparation, and high asymmetric induction.

Suggested Citation

  • Jiayin Zhang & Xihao Chang & Xianghong Xu & Hongyi Wang & Lingzi Peng & Chang Guo, 2022. "Nickel-catalyzed switchable 1,3-dienylation and enantioselective allenylation of phosphine oxides," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-34764-x
    DOI: 10.1038/s41467-022-34764-x
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