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Rhodium-Catalyzed, Remote Terminal Hydroarylation of Activated Olefins through a Long-Range Deconjugative Isomerization

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    Rhodium-Catalyzed, Remote Terminal Hydroarylation of Activated Olefins through a Long-Range Deconjugative Isomerization
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    • Arun Jyoti Borah
      Arun Jyoti Borah
      State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
      More by Arun Jyoti Borah
    • Zhuangzhi Shi*
      Zhuangzhi Shi
      State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
      *[email protected]
      More by Zhuangzhi Shi
      Orcidhttp://orcid.org/0000-0003-4571-4413
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    Cite this: J. Am. Chem. Soc. 2018, 140, 19, 6062–6066
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    https://doi.org/10.1021/jacs.8b03560
    Published May 4, 2018
    Copyright © 2018 American Chemical Society
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    Abstract

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    The Rh-catalyzed, remote terminal hydroarylation of active olefins at the C7-position of indoles and the ortho-position of indolines and anilines with the appropriate choice of a N-PtBu2 directing group through long-range deconjugative isomerization has been reported. This transformation not only overcomes the conjugate rule of Michael acceptors but also controls the positional selectivity of indoles, representing a significant advancement in both alkene isomerization and the C–H alkylation of indoles.

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    Cite this: J. Am. Chem. Soc. 2018, 140, 19, 6062–6066
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