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Heterogenized Phosphinic Acid on UiO-66-NH2: A Bifunctional Catalyst for the Synthesis of Polyhydroquinolines

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Abstract

The preparation and application of UiO-66-NH2-bis(aminomethyl)-phosphinic acid are reported in this study. The supported phosphinic acid is designed via a multi-step post-synthesis modification of a Zr-based metal–organic framework (MOF), UiO-66-NH2. The MOF is initially functionalized with ethylamine, followed by formaldehyde (formation of imine group), and finally with hypophosphorous acid to generate UiO-66-NH–CH2CH2N(CH2PO2H2)2. The modified MOF is characterized by different techniques such as XRD, SEM–EDS, FT-IR, TGA, and porosimetry. The modified MOF is efficiently used as a multifunctional heterogeneous catalyst (available Brønsted/Lewis acid sites and Lewis base site) in the multicomponent reaction of Hantzsch. A synergistic effect between the phosphinic acid and the support is observed for the synthesis of polyhydroquinolines. The catalyst is easily recycled and successfully reused several times.

Graphic Abstract

An acidic-basic heterogeneous catalyst was prepared and characterized, and the performance of the catalyst was investigated for the synthesis of polyhydroquinoline derivatives.

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Acknowledgements

The authors gratefully acknowledge Razi University for financial support.

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Authors and Affiliations

  1. Department of Organic Chemistry, Razi University, 67149-67346, Kermanshah, Iran

    Saeed Askari, Mohammad Mehdi Khodaei & Mohammad Jafarzadeh

  2. Nanoscience & Nanotechnology Research Center (NNRC), Razi University, 67149-67346, Kermanshah, Iran

    Mohammad Mehdi Khodaei & Mohammad Jafarzadeh

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  1. Saeed Askari
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  2. Mohammad Mehdi Khodaei
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  3. Mohammad Jafarzadeh
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Correspondence to Mohammad Mehdi Khodaei.

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Askari, S., Khodaei, M.M. & Jafarzadeh, M. Heterogenized Phosphinic Acid on UiO-66-NH2: A Bifunctional Catalyst for the Synthesis of Polyhydroquinolines. Catal Lett 152, 1517–1529 (2022). https://doi.org/10.1007/s10562-021-03734-1

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