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Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones

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Abstract

The aim of this work is to introduce a novel and attractive protic acidic ionic liquid as catalyst for organic synthesis. To achieve this aim, N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} was prepared by reaction of NEt3 with ClSO3H and then with H2SO4. The novel acidic ionic liquid was identified by Fourier-transform infrared (FT-IR), 1H nuclear magnetic resonance (NMR), 13C NMR, and mass spectroscopies. Its catalytic activity was then examined in the cross-aldol condensation reaction of arylaldehydes with cycloalkanones under solvent-free conditions, obtaining α,α′-bis(arylidene)cycloalkanones in high yield after short reaction time.

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Acknowledgments

The authors thank the Research Council of Payame Noor University for financial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran

    Salimeh Ahmadi, Abdolkarim Zare, Mina Aali-Hosaini, Maryam Maghsoudi, Shadi Izadpanah, Abolfath Parhami & Maria Merajoddin

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  1. Salimeh Ahmadi
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  2. Abdolkarim Zare
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  3. Mina Aali-Hosaini
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  4. Maryam Maghsoudi
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  5. Shadi Izadpanah
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  7. Maria Merajoddin
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Correspondence to Abdolkarim Zare.

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Ahmadi, S., Zare, A., Aali-Hosaini, M. et al. Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones. Res Chem Intermed 42, 6245–6253 (2016). https://doi.org/10.1007/s11164-016-2458-2

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