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Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

Author

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  • Guogang Deng

    (School of Chemical Science and Technology, Yunnan University)

  • Shengzu Duan

    (School of Chemical Science and Technology, Yunnan University)

  • Jing Wang

    (School of Chemical Science and Technology, Yunnan University)

  • Zhuo Chen

    (School of Chemical Science and Technology, Yunnan University)

  • Tongqi Liu

    (School of Chemical Science and Technology, Yunnan University)

  • Wen Chen

    (School of Chemical Science and Technology, Yunnan University)

  • Hongbin Zhang

    (School of Chemical Science and Technology, Yunnan University)

  • Xiaodong Yang

    (School of Chemical Science and Technology, Yunnan University)

  • Patrick J. Walsh

    (University of Pennsylvania)

Abstract

Allylation of nucleophiles with highly reactive electrophiles like allyl halides can be conducted without metal catalysts. Less reactive electrophiles, such as allyl esters and carbonates, usually require a transition metal catalyst to facilitate the allylation. Herein, we report a unique transition-metal-free allylation strategy with allyl ether electrophiles. Reaction of a host of allyl ethers with 2-azaallyl anions delivers valuable homoallylic amine derivatives (up to 92%), which are significant in the pharmaceutical industry. Interestingly, no deprotonative isomerization or cyclization of the products were observed. The potential synthetic utility and ease of operation is demonstrated by a gram scale telescoped preparation of a homoallylic amine. In addition, mechanistic studies provide insight into these C(sp3)–C(sp3) bond-forming reactions.

Suggested Citation

  • Guogang Deng & Shengzu Duan & Jing Wang & Zhuo Chen & Tongqi Liu & Wen Chen & Hongbin Zhang & Xiaodong Yang & Patrick J. Walsh, 2021. "Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms," Nature Communications, Nature, vol. 12(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-24027-6
    DOI: 10.1038/s41467-021-24027-6
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