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Photoredox-catalyzed oxo-amination of aryl cyclopropanes

Author

Listed:
  • Liang Ge

    (Nanjing Tech University)

  • Ding-Xing Wang

    (Nanjing Tech University)

  • Renyi Xing

    (Nanjing Tech University)

  • Di Ma

    (Nanjing Tech University)

  • Patrick J. Walsh

    (University of Pennsylvania)

  • Chao Feng

    (Nanjing Tech University)

Abstract

Cyclopropanes represent a class of versatile building blocks in modern organic synthesis. While the release of ring strain offers a thermodynamic driving force, the control of selectivity for C–C bond cleavage and the subsequent regiochemistry of the functionalization remains difficult, especially for unactivated cyclopropanes. Here we report a photoredox-coupled ring-opening oxo-amination of electronically unbiased cyclopropanes, which enables the expedient construction of a host of structurally diverse β-amino ketone derivatives. Through one electron oxidation, the relatively inert aryl cyclopropanes are readily converted into reactive radical cation intermediates, which in turn participate in the ensuing ring-opening functionalizations. Based on mechanistic studies, the present oxo-amination is proposed to proceed through an SN2-like nucleophilic attack/ring-opening manifold. This protocol features wide substrate scope, mild reaction conditions, and use of dioxygen as an oxidant both for catalyst regeneration and oxygen-incorporation. Moreover, a one-pot formal aminoacylation of olefins is described through a sequential cyclopropanation/oxo-amination.

Suggested Citation

  • Liang Ge & Ding-Xing Wang & Renyi Xing & Di Ma & Patrick J. Walsh & Chao Feng, 2019. "Photoredox-catalyzed oxo-amination of aryl cyclopropanes," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
  • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-12403-2
    DOI: 10.1038/s41467-019-12403-2
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    Cited by:

    1. Liang Ge & Chi Zhang & Chengkai Pan & Ding-Xing Wang & Dong-Ying Liu & Zhi-Qiang Li & Pingkang Shen & Lifang Tian & Chao Feng, 2022. "Photoredox-catalyzed C–C bond cleavage of cyclopropanes for the formation of C(sp3)–heteroatom bonds," Nature Communications, Nature, vol. 13(1), pages 1-13, December.
    2. Yuanli Xu & Wenlong Chen & Ruihua Pu & Jia Ding & Qing An & Yi Yang & Weimin Liu & Zhiwei Zuo, 2024. "Selective monodeuteration enabled by bisphosphonium catalyzed ring opening processes," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    3. Mingrui Li & Yingtao Wu & Xiao Song & Jiaqiong Sun & Zuxiao Zhang & Guangfan Zheng & Qian Zhang, 2024. "Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent," Nature Communications, Nature, vol. 15(1), pages 1-9, December.

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