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Reduced graphene oxide/palladium nanoparticle bonded to N,N'-bis(2-aminophenyl)-1,2-ethanediamine: a new, highly efficient and recyclable heterogeneous catalyst for direct synthesis of 2-substituted benzimidazoles via acceptorless dehydrogenative coupling of alcohols and aromatic diamine

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Abstract

In this paper, the stable synthesis of benzimidazoles catalyzed by reduced graphene oxide/palladium nanoparticle bonded to N,N'-bis(2-aminophenyl)-1,2-ethanediamine (RGO/N-ligand-Pd(0) nanocomposite) through acceptorless dehydrogenative coupling (ADC) of 1,2-phenylenediamine and benzyl alcohol is investigated. The main advantage of this report is the use of RGO/N-ligand-Pd(0) nanocomposite as a new and highly efficient heterogeneous catalyst for the synthesis of a wide range of 2-substituted benzimidazoles using the benign environmental process ADC, because in this process valuable by-products of water and hydrogen gas are produced. The prepared catalyst was identified using various techniques. The results showed that the N-ligand-Pd(0) anchored steadily to the GO nanosheets. The current method has several advantages such as short reaction time, large surface area, and high thermal stability of the catalyst, the ability to reuse the catalyst several times without significant loss of catalytic activity, and the use of benzyl alcohol as a primary material.

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Funding

The authors gratefully acknowledge the financial support provided by the Bu-Ali Sina University, Hamedan, Iran, to carry out this research.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

    Azin Kharazmi, Ramin Ghorbani-Vaghei & Arezoo Kharazmi

  2. Department of Inorganic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

    Reza Azadbakht

  3. Department of Inorganic Chemistry, Faculty of Chemistry, Ilam University, Ilam, 69315516, Iran

    Mostafa Koolivand

  4. Department of Chemistry, College of Basic Sciences, Gebze Technical University, 41400, Gebze, Turkey

    Idris Karakaya

  5. Department of Chemistry, Faculty of Science, University of Maragheh, P.O Box 55181-83111, Maragheh, Iran

    Rahman Karimi-Nami

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  1. Azin Kharazmi
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Contributions

AK involved in conceptualization, methodology, resources, writing—original draft, reviewing and editing, formal analysis. RG-V took part in conceptualization, visualization, investigation, supervision, writing—review and editing. AK involved in software, formal analysis, reviewing and editing. RA involved in data curation, formal analysis. MK: visualization, software. IK took part in data curation, formal analysis. RK-N involved in data curation and formal analysis.

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Correspondence to Ramin Ghorbani-Vaghei.

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Kharazmi, A., Ghorbani-Vaghei, R., Kharazmi, A. et al. Reduced graphene oxide/palladium nanoparticle bonded to N,N'-bis(2-aminophenyl)-1,2-ethanediamine: a new, highly efficient and recyclable heterogeneous catalyst for direct synthesis of 2-substituted benzimidazoles via acceptorless dehydrogenative coupling of alcohols and aromatic diamine. Res Chem Intermed 49, 2277–2298 (2023). https://doi.org/10.1007/s11164-023-05003-9

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