Iodine-catalyzed regioselective C-3 arylation of indoles with p-quinols

Abstract

Iodine-mediated highly convenient strategy for the C-3 arylation of indoles with p-quinols is presented. The present work surpasses in forming a C–C bond at the meta-position of the phenols, which is traditionally challenging to functionalize. This protocol further leads the way to have ascendable, forthright access to phenol-assimilated heterocycles which have powerful applications both in synthetic and medicinal chemistry.

Graphic abstract

Iodine-mediated highly convenient and rapid protocol for C-3 arylation of indoles with p-quinols is presented. This methodology utilizes readily available indoles, furans and thiophene for Michael addition to p-quinols and subsequent aromatization to access phenol-assimilated heterocycles which have powerful applications both in synthetic and medicinal chemistry.

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Acknowledgements

We thank the Department of Science Technology (DST) for providing HRMS facility in the FIST program, and ND thanks the MHRD, New Delhi for a research fellowship.

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Correspondence to Rama Krishna Peddinti.

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Dua, N., Peddinti, R.K. Iodine-catalyzed regioselective C-3 arylation of indoles with p-quinols. J Chem Sci 132, 45 (2020). https://doi.org/10.1007/s12039-020-1742-2

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Keywords

  • C-3 arylation of indoles
  • meta-functionalized phenols
  • indole-phenol hybrids
  • regioselective reaction