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Photocatalytic divergent decarboxylative amination: a metal-free access to aliphatic amines and hydrazines

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Abstract

Nitrogen-containing motifs are widely present in natural products, bioactive molecules, and drugs. Accordingly, effective synthetic methods with high efficiency and diversity are highly desirable. Here, we present the invention of a facile, visible light-mediated decarboxylative C(sp3)-N bond-forming reaction by employing abundant carboxylic acids as the feedstock and a commercial diazirine as a nitrogen donor. This process is amenable to access both imines and diaziridines, as the corresponding masked amines and hydrazines, through a selectable single or double nitrogen transfer from the diazirine, respectively. This divergent approach works well in both directions with various alkyl carboxylic acids, including primary, secondary, and tertiary acids, as well as natural products and drugs, thus affording a rapid, metal-free approach to build nitrogen-containing molecule libraries with considerable structural diversity, which could thus benefit the related study in context of chemical biology and drug discovery.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21602028), Beijing National Laboratory for Molecular Sciences (BNLMS201913), the Recruitment Program of Global Experts, and Fuzhou University.

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Authors and Affiliations

  1. Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, 350108, China

    Xianli Shu, Ruting Xu & Saihu Liao

  2. Beijing National Laboratory for Molecular Sciences, Beijing, 100190, China

    Saihu Liao

Authors
  1. Xianli Shu
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  2. Ruting Xu
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  3. Saihu Liao
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Correspondence to Saihu Liao.

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The authors declare no conflict of interest.

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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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Shu, X., Xu, R. & Liao, S. Photocatalytic divergent decarboxylative amination: a metal-free access to aliphatic amines and hydrazines. Sci. China Chem. 64, 1756–1762 (2021). https://doi.org/10.1007/s11426-021-1048-4

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  • DOI: https://doi.org/10.1007/s11426-021-1048-4

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