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Silica-supported antimony(III) chloride as a mild and reusable catalyst for the Paal–Knorr pyrrole synthesis

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Abstract

Heterogeneous catalysts are used for control of environmental pollution. Heterogeneous catalysts are easily separated from the reaction mixture, thus allowing their recovery and re-use. There is a need for catalysts that are efficient under mild conditions. Here, we show that silica-supported antimony(III) chloride (SbCl3/SiO2) acts as a highly efficient heterogeneous Lewis acid catalyst for the Paal–Knorr pyrrole synthesis at room temperature. We found that condensation of hexane-2,5-dione with aromatic and aliphatic primary amines in hexane using SbCl3/SiO2 with 7.6 wt% SbCl3 was the best reaction condition. The silica support facilitated the workup of the reaction mixture and provided a reusable catalyst at least for 7 runs without significant loss in activity. Indeed, the yield was 98% for the first run and 84% for the 7th run. We conclude that low catalyst loading, operational simplicity, practicability and applicability to various substrates make this reaction an interesting alternative to previously applied procedures. From the environmental standpoint, this eco-friendly catalyst is stable, highly active, easy to prepare and handle.

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Authors and Affiliations

  1. Chemistry and Chemical Engineering Research Center of Iran, Pajoohesh Blvd., km 17, Karaj Hwy, 14968-13151, Tehran, Iran

    Hossein Reza Darabi, Kioumars Aghapoor, Farshid Mohsenzadeh, Nazafarin Asadollahnejad, Hossein Taherzadeh & Yadollah Balavar

  2. Department of Chemistry, Payame Noor University (PNU), Abhar, Iran

    Mohammad Reza Poorheravi & Asyeh Mirzaee

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  1. Hossein Reza Darabi
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  2. Mohammad Reza Poorheravi
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  3. Kioumars Aghapoor
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  4. Asyeh Mirzaee
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  5. Farshid Mohsenzadeh
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  6. Nazafarin Asadollahnejad
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  7. Hossein Taherzadeh
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  8. Yadollah Balavar
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Correspondence to Hossein Reza Darabi.

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Darabi, H.R., Poorheravi, M.R., Aghapoor, K. et al. Silica-supported antimony(III) chloride as a mild and reusable catalyst for the Paal–Knorr pyrrole synthesis. Environ Chem Lett 10, 5–12 (2012). https://doi.org/10.1007/s10311-011-0321-7

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  • DOI: https://doi.org/10.1007/s10311-011-0321-7

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