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Synthesis of indenoquinolinone through aryne-mediated Pd(II)-catalysed remote C–H activation

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Abstract

Indenoquinolinones have been synthesized from 2-haloquinoline-3-carbaldehyde through Pd-mediated simultaneous C–H (aldehyde) and C–X bond activation. DFT studies were performed to investigate the mechanistic pathway, and in situ UV–Vis studies indicate the presence of Pd(II) intermediate species. Aryne ligated Pd complex is actual intermediate in these reactions. Ligation of reactive aryne to Pd reduces probability of side reactions.

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Acknowledgements

Authors are thankful to Dr. N.K.Shah, Head, Department of Chemistry, Gujarat University, for laboratory facilities and Department of Chemistry, PDPU, for providing computational facilities and NFDD Centre, Rajkot, for spectral analysis.

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Authors and Affiliations

  1. Department of Chemistry, Gujarat University, Ahmedabad, Gujarat, 380009, India

    Anuj P. Patel & Mohammedumar M. Shaikh

  2. Chemical Department, VGEC, Ahmedabad, Gujarat, 382424, India

    Kamlesh K. Gurjar

  3. Department of Chemistry, Veer Narmad South Gujarat University, Surat, Gujarat, 395007, India

    Kishor H. Chikhalia

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  1. Anuj P. Patel
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  2. Mohammedumar M. Shaikh
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  4. Kishor H. Chikhalia
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Correspondence to Kishor H. Chikhalia.

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Patel, A.P., Shaikh, M.M., Gurjar, K.K. et al. Synthesis of indenoquinolinone through aryne-mediated Pd(II)-catalysed remote C–H activation. Res Chem Intermed 47, 2049–2061 (2021). https://doi.org/10.1007/s11164-020-04387-2

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