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Photoinduced and palladium-catalyzed hydrogen atom transfer triggered 1,2-difunctionalization of 1,3-dienes with hydroxamides

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Abstract

The discovery of novel catalysis modes to generate a significant increase in structural complexity from readily available reactants is a fundamental goal in modern organic synthesis. Here, we report a photoinduced palladium-catalyzed hydrogen atom transfer triggered 1,2-difunctionalization of conjugated dienes. Without the employment of exogeneous photosensitizers and external oxidants, the cascade reaction realized the integration of remote functionalization of various C(sp3)-H bonds and selective difunctionalization of 1,3-dienes with 100% atom efficiency, allowing for the synthesis of structurally diverse amides with up to 90% yields. Given the prevalence of amides in pharmaceuticals and natural products, the current protocol has provided an efficient means to access highly functionalized amides from readily available carboxylic acid derivatives and 1,3-dienes.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22188101, 21831007, 21971231, 21772184).

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China

    Xiao-Yun Ruan, Tao Zhang, Wen-Ao Li, Yi-Zhuo Yin, Zhi-Yong Han & Liu-Zhu Gong

Authors
  1. Xiao-Yun Ruan
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  2. Tao Zhang
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  3. Wen-Ao Li
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  4. Yi-Zhuo Yin
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  5. Zhi-Yong Han
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  6. Liu-Zhu Gong
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Corresponding authors

Correspondence to Zhi-Yong Han or Liu-Zhu Gong.

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Supporting information The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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11426_2022_1236_MOESM1_ESM.pdf

Photoinduced and Palladium-Catalyzed Hydrogen Atom Transfer Triggered 1,2-Difunctionalization of 1,3-Dienes with Hydroxamides

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Ruan, XY., Zhang, T., Li, WA. et al. Photoinduced and palladium-catalyzed hydrogen atom transfer triggered 1,2-difunctionalization of 1,3-dienes with hydroxamides. Sci. China Chem. 65, 863–869 (2022). https://doi.org/10.1007/s11426-022-1236-y

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  • DOI: https://doi.org/10.1007/s11426-022-1236-y

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