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Photoredox Mediated Acceptorless Dehydrogenative Coupling of Saturated N-Heterocycles

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    Research Article

    Photoredox Mediated Acceptorless Dehydrogenative Coupling of Saturated N-Heterocycles
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    • Zongbin Jia
      Zongbin Jia
      Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China, 100190
      School of Chemical Science, University of Chinese Academy of Sciences, Beijing, China, 100049
      More by Zongbin Jia
    • Qi Yang
      Qi Yang
      Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China, 100190
      School of Chemical Science, University of Chinese Academy of Sciences, Beijing, China, 100049
      More by Qi Yang
    • Long Zhang
      Long Zhang
      Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China, 100190
      Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing, China, 100084
      More by Long Zhang
    • Sanzhong Luo*
      Sanzhong Luo
      Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China, 100190
      Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing, China, 100084
      *E-mail: [email protected]
      More by Sanzhong Luo
      Orcidhttp://orcid.org/0000-0001-8714-4047
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    ACS Catalysis

    Cite this: ACS Catal. 2019, 9, 4, 3589–3594
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    https://doi.org/10.1021/acscatal.9b00123
    Published March 14, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    We report herein a direct unsymmetric coupling and controllable aromatization reaction of saturated N-heterocycles enabled by synergistic photoredox and acid catalysis. The reaction furnishes C2–C3 connected biheterocycles in a highly chemo- and regioselective manner under rather mild conditions. Mechanistic studies indicated that the reaction proceeded via enamine-iminium coupling leading to exclusively C2–C3 connection.

    Copyright © 2019 American Chemical Society

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    Cited By

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    ACS Catalysis

    Cite this: ACS Catal. 2019, 9, 4, 3589–3594
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acscatal.9b00123
    Published March 14, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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