Polythiophene‐functionalized magnetic carbon nanotube-supported copper(I) complex: a novel and retrievable heterogeneous catalyst for the “Phosphine- and Palladium-Free” Suzuki–Miyaura cross-coupling reaction

Abstract

A simple preparation of catalysts with high catalytic activity and superior cycling stability is very desirable. In this contribution, magnetic carbon nanotube functionalized by polythiophene (CNT–Fe3O4–PTh) acts as an efficient and retrievable host for copper nanoparticles to prepare CNT–Fe3O4–PTh–Cu(I) as a nontoxic and inexpensive catalyst. FT-IR, TGA, EDX, VSM, XRD, FE-SEM, TEM, and AAS techniques were employed to characterize the structure of the synthesized magnetic heterogeneous nanocomposite. Thereafter, the catalytic application of the catalyst was evaluated for the phosphine- and palladium-free Suzuki–Miyaura cross-coupling reaction in water/ethanol as a green media in short reaction times with good to excellent yields. Various derivatives of biaryl compounds were synthesized by reaction of aryl halides and phenylboronic acid. Simple methodology and easy workup, short reaction times, elimination of volatile and toxic solvents, biocompatible reaction conditions, and high yields are some advantages of this protocol. Moreover, the catalyst showed a good reusability owing to its magnetic properties and was recycled several times without appreciable decrease in its catalytic efficiency.

Graphic abstract

Copper(I) nanoparticles supported on magnetic carbon nanotube functionalized by polythiophene (CNT–Fe3O4–PTh–Cu(I)), was prepared and used for ligand- and palladiumfree Suzuki–Miyaura cross-coupling reaction in water/ethanol as a green media in short reaction times with good to excellent yields. Reusability and stability tests demonstrated that the as prepared catalyst can be recycled with a negligible loss of its activity.

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Acknowledgements

The authors gratefully acknowledge the Research Council of the Semnan University for the financial support of this work.

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Correspondence to Nadiya Koukabi.

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Akbarzadeh, P., Koukabi, N. & Kolvari, E. Polythiophene‐functionalized magnetic carbon nanotube-supported copper(I) complex: a novel and retrievable heterogeneous catalyst for the “Phosphine- and Palladium-Free” Suzuki–Miyaura cross-coupling reaction. Mol Divers 24, 1125–1137 (2020). https://doi.org/10.1007/s11030-019-10016-x

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Keywords

  • Carbon nanotube
  • Copper(I) nanocomposite
  • Magnetic nanoparticles
  • Polythiophene
  • Suzuki–Miyaura cross-coupling reaction