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An unsymmetrical Schiff-base derived recyclable Pd-catalyst for Suzuki–Miyaura and Sonogashira reactions in aqueous media

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Abstract

A water-soluble palladium (II) complex containing an unsymmetrical Schiff-base ligand was synthesized and applied as catalyst Suzuki–Miyaura and Sonogashira cross-coupling reactions in aqueous media. Notably, moderate to excellent yields of biaryls were obtained in Suzuki reaction with usually less reactive aryl and heteroaryl chlorides under relatively mild condition. Moderate-to-high yields of aryl-alkynes were also obtained in Sonogashira reactions using aryl bromides. Apart from hydrophilic nature, the accomplishment of reactions in water, high recyclability, broad functional group tolerance, etc., are other advantages of the system.

Graphic abstract

This work presents a water–soluble palladium (II)–Schiff–base catalyst for aqueous Suzuki–Miyaura and Sonogashira reactions. It could accelerate both the reactions producing moderate to excellent yields of desired products under relatively greener reaction conditions. The catalyst could also be recycled upto four cycles in both the reactions

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Acknowledgement

DST, New Delhi is gratefully acknowledged for financial support (Grant nos. 2015/000021 and CRG/2018/001669) and UGC, New Delhi for SAP-DRS programme. The authors also acknowledge the NMR Research Centre, IISc, Bangalore and SAIF, Punjab University, Chandigarh for NMR and ESI-MS analyses respectively.

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Author notes

  1. Achinta Gogoi

    Present address: Department of Chemistry, North-Eastern Hill University, Shillong, Meghalaya, 793022, India

Authors and Affiliations

  1. Department of Chemistry, Dibrugarh University, Dibrugarh, Assam, 786004, India

    Amlan Puzari, Achinta Gogoi & Pankaj Das

Authors
  1. Amlan Puzari
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  2. Achinta Gogoi
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  3. Pankaj Das
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Correspondence to Pankaj Das.

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Puzari, A., Gogoi, A. & Das, P. An unsymmetrical Schiff-base derived recyclable Pd-catalyst for Suzuki–Miyaura and Sonogashira reactions in aqueous media. J Chem Sci 133, 56 (2021). https://doi.org/10.1007/s12039-021-01909-2

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  • DOI: https://doi.org/10.1007/s12039-021-01909-2

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