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Visible-light promoted regioselective amination and alkylation of remote C(sp3)-H bonds

Author

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  • Quanping Guo

    (Lanzhou University)

  • Qiang Peng

    (Lanzhou University)

  • Hongli Chai

    (Lanzhou University)

  • Yumei Huo

    (Lanzhou University)

  • Shan Wang

    (Lanzhou University)

  • Zhaoqing Xu

    (Lanzhou University)

Abstract

The C-N cross coupling reaction has always been a fundamental task in organic synthesis. However, the direct use of N-H group of aryl amines to generate N-centered radicals which would couple with alkyl radicals to construct C-N bonds is still rare. Here we report a visible light-promoted C-N radical cross coupling for regioselective amination of remote C(sp3)-H bonds. Under visible light irradiation, the N-H groups of aryl amines are converted to N-centered radicals, and are then trapped by alkyl radicals, which are generated from Hofmann-Löffler-Freytag (HLF) type 1,5-hydrogen atom transfer (1,5-HAT). With the same strategy, the regioselective C(sp3)-C(sp3) cross coupling is also realized by using alkyl Hantzsch esters (or nitrile) as radical alkylation reagents. Notably, the α-C(sp3)-H of tertiary amines can be directly alkylated to form the C(sp3)-C(sp3) bonds via C(sp3)-H − C(sp3)-H cross coupling through the same photoredox pathway.

Suggested Citation

  • Quanping Guo & Qiang Peng & Hongli Chai & Yumei Huo & Shan Wang & Zhaoqing Xu, 2020. "Visible-light promoted regioselective amination and alkylation of remote C(sp3)-H bonds," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-15167-2
    DOI: 10.1038/s41467-020-15167-2
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    Cited by:

    1. Chunyang Zhao & Yang Li & Yujiao Dong & Miao Li & Dan Xia & Shuangqiu Gao & Qian Zhang & Qun Liu & Wei Guan & Junkai Fu, 2022. "Divergent regioselective Heck-type reaction of unactivated alkenes and N-fluoro-sulfonamides," Nature Communications, Nature, vol. 13(1), pages 1-16, December.
    2. Chunyang Zhao & Rongwan Gao & Wenxuan Ma & Miao Li & Yifei Li & Qian Zhang & Wei Guan & Junkai Fu, 2024. "A facile synthesis of α,β-unsaturated imines via palladium-catalyzed dehydrogenation," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    3. Yulin Zhang & Yoshiaki Tanabe & Shogo Kuriyama & Ken Sakata & Yoshiaki Nishibayashi, 2023. "Interplay of diruthenium catalyst in controlling enantioselective propargylic substitution reactions with visible light-generated alkyl radicals," Nature Communications, Nature, vol. 14(1), pages 1-16, December.

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