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An efficient TBHP/TBAI-mediated protocol for the synthesis of 4H-chromen-4-ones from chroman-4-ones via oxidative C–C bond formation

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Abstract

A transition metal-free and efficient TBHP/TBAI-mediated protocol has been developed for the synthesis of 4H-chromen-4-ones from chroman-4-ones via oxidative C–C bond formation. It proceeds in the presence of a catalytic amount of tetrabutylammonium iodide and oxidant tert-butyl hydroperoxide (TBHP, 5–6 M in decane) to afford the corresponding products in good to excellent yields. Furthermore, it has been observed that an increase in the concentration of TBHP to 30 mol % drastically increases the yield of 4H-chromen-4-ones, any further increase will lead to a decrease in percent yield. The mechanism of this reaction involves the generation of tertiary butoxide radical initially which by oxidative single-electron transformation is converted to iodochroman-4-one. Later the hydrogen iodide is removed from iodochroman-4-one to give the desired product, i.e. 4H-chromen-4-ones. Moreover, this is a rare example of the n-Bu4NI/TBHP-mediated C–C bond through dehydrogenative reaction.

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Acknowledgements

The authors thank Wachemo University, Ethiopia, for financial support to Dr. Habtamu Abebe Agisho and Dr. Suboot Hairat. Also the author Dr. Mehvash Zaki is highly grateful to King Abdulaziz University.

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Authors and Affiliations

  1. Department of Chemistry, Wachemo University, P.O. Box 667, Hosanna, Ethiopia

    Habtamu Abebe Agisho

  2. Department of Biotechnology, Wachemo University, P.O. Box 667, Hosanna, Ethiopia

    Suboot Hairat

  3. Department of Chemistry, King Abdulaziz University, P.O. Box 80203, Jeddah, Saudi Arabia

    Mehvash Zaki

Authors
  1. Habtamu Abebe Agisho
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  2. Suboot Hairat
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  3. Mehvash Zaki
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Correspondence to Habtamu Abebe Agisho.

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Agisho, H.A., Hairat, S. & Zaki, M. An efficient TBHP/TBAI-mediated protocol for the synthesis of 4H-chromen-4-ones from chroman-4-ones via oxidative C–C bond formation. Monatsh Chem 151, 599–603 (2020). https://doi.org/10.1007/s00706-020-02576-8

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  • DOI: https://doi.org/10.1007/s00706-020-02576-8

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