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Iodine-catalyzed \(\hbox {sp}^{3}\) C–H bond activation by selenium dioxide: synthesis of diindolylmethanes and di(3-indolyl)selanides

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Abstract

An efficient reaction protocol was developed for the synthesis of several diindolylmethane derivatives via the \(\hbox {sp}^{3}\) C–H bond activation of aryl methyl ketones by \(\hbox {SeO}_{2}\) and indoles in the presence of catalytic amounts of \(\hbox {I}_{2}\) at 80 \(^{\circ }\hbox {C}\) using dioxane as solvent. Unexpectedly, an interesting class of di(3-indolyl)selenide compounds was isolated when the reaction was carried out at room temperature.

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Acknowledgments

We thank the CSIR, New Delhi for financial assistance (CAAF-NE project). SM thanks the CSIR, New Delhi for the Senior Research Fellowship (SRF) grant and PSN thanks the UGC, New Delhi for the Senior Research Fellowship.

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Authors and Affiliations

  1. Medicinal Chemistry Division, CSIR-North East Institute of Science & Technology, Jorhat, 785006, Assam, India

    P. Seetham Naidu, Swarup Majumder & Pulak J. Bhuyan

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  1. P. Seetham Naidu
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  2. Swarup Majumder
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  3. Pulak J. Bhuyan
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Correspondence to Pulak J. Bhuyan.

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Naidu, P.S., Majumder, S. & Bhuyan, P.J. Iodine-catalyzed \(\hbox {sp}^{3}\) C–H bond activation by selenium dioxide: synthesis of diindolylmethanes and di(3-indolyl)selanides. Mol Divers 19, 685–693 (2015). https://doi.org/10.1007/s11030-015-9605-3

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