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Acceptorless dehydrogenative amination of alkenes for the synthesis of N-heterocycles

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An Erratum to this article was published on 20 September 2022

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Abstract

Catalytic amination of alkenes is one of the most attractive reactions for the construction of complex heterocycles with nitrogen centers. Herein, we present that synergistic photoredox and cobaloxime catalysis allows for highly efficient and mild dehydrogenative reactions between various NH nucleophiles and di-, tri-, and tetrasubstituted alkenes in the absence of external oxidants, thus enabling access to an array of N-heterocycles. Notably, both Z- and E-alkene-containing N-heterocycles are accessible. Mechanistic studies indicated that the Z-cinnamyl derivatives could be generated by photocatalytic E to Z alkene isomerization through an energy transfer process. Moreover, we find that sluggish energy transfer could inhibit the E to Z alkene isomerization process, thus offering the cinnamyl derivatives with E-selectivity. Our results highlight the benefits of the reactions using dual photoredox and cobaloxime catalysis to lead to diverse N-heterocycles.

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Acknowledgements

This work was supported by the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (18KJA350001) and the Priority Academic Program Development of the Jiangsu Higher Education Institutes (PAPD).

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Authors and Affiliations

  1. Jiangsu Key Laboratory of Neuropsychiatric Diseases and Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Soochow University, Suzhou, 215123, China

    Jia-Lin Tu, Wan Tang, Shi-Hui He, Ma Su & Feng Liu

  2. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

    Feng Liu

Authors
  1. Jia-Lin Tu
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  2. Wan Tang
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  3. Shi-Hui He
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  4. Ma Su
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  5. Feng Liu
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Corresponding author

Correspondence to Feng Liu.

Additional information

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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The authors declare no conflict of interest.

The online version of the original article can be found at https://doi.org/10.1007/s11426-022-1393-1

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Tu, JL., Tang, W., He, SH. et al. Acceptorless dehydrogenative amination of alkenes for the synthesis of N-heterocycles. Sci. China Chem. 65, 1330–1337 (2022). https://doi.org/10.1007/s11426-022-1241-x

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