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Selective coupling of carbon dioxide and epoxystyrene via salicylaldimine-, thiophenaldimine-, and quinolinaldimine-iron(II), iron(III), chromium(III), and cobalt(III)/Lewis base catalysts

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Abstract

A series of chromium(III)-, cobalt(III)-, and iron(III)-based complexes of the general formula [(N∩O)2MCl] (1–7) (N∩O: N-salicylidene(R)amine, R = 1-naphthyl or cyclohexyl) have been applied as catalysts for the coupling reaction of carbon dioxide and epoxystyrene (styrene oxide) in the presence of tetrabutylammonium bromide (Bu4NBr) as a cocatalyst. The reactions were carried out under relatively low pressure and solvent-free conditions. In addition, iron complexes (8–10) containing the ligands, N′-(thiophene-2-methylene)benzene-1,2-diamine, (8), N′-(quinoline-2-methylene)benzene-1,2-diamine (9), and sodium N-(4-sulfonato-salicylidene)-1,2-phenylenediamine (10) were also utilized for the catalytic reaction. The influence of metal center, ligand, temperature, and reaction time on the coupling reaction was investigated. The catalyst systems proved to be selective in the coupling reaction of CO2 and styrene oxide, resulting in cyclic styrene carbonate. In general, the iron(III)- and cobalt(III)-based catalysts bearing the aromatic 1-naphthyl terminal groups showed the highest catalytic activity under similar reaction conditions.

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Acknowledgments

Financial support by the Hashemite University and the German research Foundation (DFG) is gratefully acknowledged. We also would like to thank Prof. Dr. Dr. h. c. Bernhard Rieger, WACKER-Lehrstuhl für Makromolekulare Chemie, Department Chemie, Technische, Universität München for the helpful discussion.

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Authors and Affiliations

  1. Department of Chemistry, Hashemite University, P.O. Box 150459, Zarqa, 13115, Jordan

    Mahmoud Sunjuk, Adnan S. Abu-Surrah, Esraa Al-Ramahi & Abdullah Saleh

  2. WACKER-Lehrstuhl für Makromolekulare Chemie, Technische Universität München, Lichtenbergstraße 4, 85747, Garching bei München, Germany

    Abdussalam K. Qaroush

Authors
  1. Mahmoud Sunjuk
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  2. Adnan S. Abu-Surrah
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  3. Esraa Al-Ramahi
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  4. Abdussalam K. Qaroush
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  5. Abdullah Saleh
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Correspondence to Adnan S. Abu-Surrah.

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Sunjuk, M., Abu-Surrah, A.S., Al-Ramahi, E. et al. Selective coupling of carbon dioxide and epoxystyrene via salicylaldimine-, thiophenaldimine-, and quinolinaldimine-iron(II), iron(III), chromium(III), and cobalt(III)/Lewis base catalysts. Transition Met Chem 38, 253–257 (2013). https://doi.org/10.1007/s11243-012-9685-1

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  • DOI: https://doi.org/10.1007/s11243-012-9685-1

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