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Highly efficient, recyclable cerium-phosphate solid acid catalysts for the synthesis of tetrahydrocarbazole derivatives by Borsche–Drechsel cyclization

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Abstract

In this work, a series of cerium phosphate catalysts with different cerium phosphate molar ratios have been synthesized. The prepared catalysts were characterized by means of FTIR, DTA, TGA, XRD, N2 adsorption–desorption and SEM. Also, the acidic centers of the prepared catalysts were abundantly studied and characterized in terms of type and strength using different techniques. The characterization tools used explained the variety of acidic centers in terms of type and strength due to the variation of cerium to phosphate molar ratio. Its worthy to mentioned that the highly acidic performance of the prepared catalysts was successfully applied in the synthesis of tetrahydrocarbazoles derivatives via Borsche–Drechsel cyclization reaction. The catalysts showed great catalytic activity in the selected reaction as high product yields were obtained using a very small amount of the catalysts under mild reaction conditions. The % yield and the reaction mechanism proves the role played by Brønsted acid sites of the catalyst in indorsing the reaction. The results also demonstrated a high ability of the catalysts to be reused ten times without a significant decrease in the catalytic activity. The synthesized tetrahydrocarbazole derivatives via heterogenous acid-catalyzed Borsche–Drechsel cyclization reaction can be considered as highly efficient and eco-friendly strategy towards many other carbazoles and open a new era in green chemistry as well.

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Acknowledgements

The authors are highly indebted to the Deanship of the Scientific Research (DSR), Umm Al-Qura University for the financial support through the Project Number 19-SCI-1-01-0010.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Applied Science, Umm Al-Qura University, Makkah, 21955, Saudi Arabia

    Hatem M. Altass, Abdelrahman S. Khder, Saleh A. Ahmed, Moataz Morad & Abdullah A. Alsabei

  2. Research Laboratories Unit, Faculty of Applied Science, Umm Al-Qura University, Makkah, 21955, Saudi Arabia

    Hatem M. Altass, Abdelrahman S. Khder, Saleh A. Ahmed, Moataz Morad, Abdullah A. Alsabei & Khalid Althagafy

  3. Faculty of Science, Chemistry Department, Mansoura University, Mansoura, 35516, Egypt

    Abdelrahman S. Khder & Awad I. Ahmed

  4. Chemistry Department, Faculty of Science, Assiut University, Assiut, 71516, Egypt

    Saleh A. Ahmed

  5. Department of Chemistry, Jamoum University College, Umm Al-Qura University, Makkah, 21955, Saudi Arabia

    Rabab S. Jassas

  6. Physics Department, Faculty of Applied Science, Umm Al-Qura University, Makkah, 21955, Saudi Arabia

    Khalid Althagafy

  7. Basic Science Department, Faculty of Engineering, Delta University for Science and Technology, Gamasa, Egypt

    Reda S. Salama

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  1. Hatem M. Altass
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  2. Abdelrahman S. Khder
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Correspondence to Abdelrahman S. Khder.

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Altass, H.M., Khder, A.S., Ahmed, S.A. et al. Highly efficient, recyclable cerium-phosphate solid acid catalysts for the synthesis of tetrahydrocarbazole derivatives by Borsche–Drechsel cyclization. Reac Kinet Mech Cat 134, 143–161 (2021). https://doi.org/10.1007/s11144-021-02050-4

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