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Visible light-triggered selective C(sp2)-H/C(sp3)-H coupling of benzenes with aliphatic hydrocarbons

Author

Listed:
  • Qian-Yu Li

    (Xiamen University)

  • Shiyan Cheng

    (Xiamen University)

  • Ziqi Ye

    (Xiamen University)

  • Tao Huang

    (Xiamen University)

  • Fuxing Yang

    (Xiamen University)

  • Yu-Mei Lin

    (Xiamen University)

  • Lei Gong

    (Xiamen University
    Innovation Laboratory for Sciences and Technologies of Energy Materials of Fujian Province (IKKEM))

Abstract

The direct and selective coupling of benzenes with aliphatic hydrocarbons is a promising strategy for C(sp2)-C(sp3) bond formation using readily available starting materials, yet it remains a significant challenge. In this study, we have developed a simplified photochemical system that incorporates catalytic amounts of iron(III) halides as multifunctional reagents and air as a green oxidant to address this synthetic problem. Under mild conditions, the reaction between a strong C(sp2)-H bond and a robust C(sp3)-H bond has been achieved, affording a broad range of cross-coupling products with high yields and commendable chemo-, site-selectivity. The iron halide acts as a multifunctional reagent that responds to visible light, initiates C-centered radicals, induces single-electron oxidation to carbocations, and participates in a subsequent Friedel-Crafts-type process. The gradual release of radical species and carbocation intermediates appears to be critical for achieving desirable reactivity and selectivity. This eco-friendly, cost-efficient approach offers access to various building blocks from abundant hydrocarbon feedstocks, and demonstrates the potential of iron halides in sustainable synthesis.

Suggested Citation

  • Qian-Yu Li & Shiyan Cheng & Ziqi Ye & Tao Huang & Fuxing Yang & Yu-Mei Lin & Lei Gong, 2023. "Visible light-triggered selective C(sp2)-H/C(sp3)-H coupling of benzenes with aliphatic hydrocarbons," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-42191-9
    DOI: 10.1038/s41467-023-42191-9
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    References listed on IDEAS

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    1. Shi Cao & Wei Hong & Ziqi Ye & Lei Gong, 2021. "Photocatalytic three-component asymmetric sulfonylation via direct C(sp3)-H functionalization," Nature Communications, Nature, vol. 12(1), pages 1-12, December.
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    3. Kuangbiao Liao & Solymar Negretti & Djamaladdin G. Musaev & John Bacsa & Huw M. L. Davies, 2016. "Site-selective and stereoselective functionalization of unactivated C–H bonds," Nature, Nature, vol. 533(7602), pages 230-234, May.
    4. Cheng, Feng & Brewer, Catherine E., 2017. "Producing jet fuel from biomass lignin: Potential pathways to alkyl-benzenes and cycloalkanes," Renewable and Sustainable Energy Reviews, Elsevier, vol. 72(C), pages 673-722.
    5. Chia-Yu Huang & Jianbin Li & Chao-Jun Li, 2021. "A cross-dehydrogenative C(sp3)−H heteroarylation via photo-induced catalytic chlorine radical generation," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
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