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Carbon Dioxide Cycloaddition to Epoxides: A Comparative Study on the Catalytic Activities of Two Binary Catalysts VIVO(N2O2)/TBAB and VVO2(O2N)/TBAB and In Situ Derivation of a Bifunctional Catalyst

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Abstract

A comparative study is illustrated on the catalytic activities of two structurally very different vanadium complexes, one oxovanadium(IV) complex 1, VIVO(N2O2) and the other dioxovanadium(V) complex 2, VVO2(O2N) for the carbon dioxide cycloaddition to epoxides to yield cyclic carbonates. The binary catalyst, 1/TBAB is found to be non-selective towards the size of the epoxide substrates showing 90–100% conversions to cyclic carbonate products under the reaction conditions [60 °C, 5 bar (pCO2),  4 h]. However, the other binary catalyst, 2/TBAB having bulky tetrabutylammonium counter cation, could show selectivity resulting only 52% (allyl glycidyl ether), 63% (butyl glycidyl ether) and 54% (1-hexene oxide) conversions for longer tailed epoxides, on contrary to the  99% (epibromohydrin) and  88% (epichlorohydrin) conversions for shorter tailed epoxides. Further, taking the advantage of the modifiability of bromo functional group to imidazolium bromide functionality, the bromo functional group containing oxovanadium(IV) complex 1 has been affixed with imidazolium bromide functionality on reaction with N-methyl imidazole, and thus transformed to a bifunctional catalyst, 1A•Br. This in situ formed bifunctional catalyst, 1A•Br during the course of catalytic reaction, also showed to be an active catalyst system resulting in 100% conversion under the reaction conditions [60 °C, 5 bar (pCO2), 12 h].

Graphical Abstract

VIVO(N2O2) shows no substrate discrimination in the cycloaddition of CO2 to epoxides, while anionic VVO2(O2N) having bulky tetrabutyl ammonium counter cation shows. Low conversions to cyclic carbonates are found for epoxides with longer tails compared to shorter tailed ones, when VVO2(O2N) is employed as a catalyst component. In situ modification of bromo functionalised ligand containing complex VIVO(N2O2) to a bifunctional catalyst via introducing imidazoliumbromide functionalities.

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Acknowledgements

We thank DST-SERB, New Delhi, India for financial support. RB thanks CSIR for the research fellowship. We also thank the Department of Chemistry, Gauhati University for various facilities and Sophisticated Analytical Instrumentation Facility (SAIF), Gauhati University for the single crystal X-ray diffraction facility.

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  1. Department of Chemistry, Gauhati University, Guwahati, Assam, 781014, India

    Rakhimoni Borah, Naranarayan Deori, Surabhi Lahkar, Saurav Paul & Sanfaori Brahma

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  1. Rakhimoni Borah
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  2. Naranarayan Deori
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  3. Surabhi Lahkar
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  4. Saurav Paul
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  5. Sanfaori Brahma
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Contributions

RB: data curation, methodology, investigation, validation, visualization and writing—original draft. ND: software. SL: validation. SP: software and investigation. SB: conceptualization, funding acquisition, project administration, supervision and resources.

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Correspondence to Sanfaori Brahma.

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Borah, R., Deori, N., Lahkar, S. et al. Carbon Dioxide Cycloaddition to Epoxides: A Comparative Study on the Catalytic Activities of Two Binary Catalysts VIVO(N2O2)/TBAB and VVO2(O2N)/TBAB and In Situ Derivation of a Bifunctional Catalyst. Catal Lett 154, 1081–1093 (2024). https://doi.org/10.1007/s10562-023-04367-2

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