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Regenerated cellulose supported palladium composite superfine fibers as an efficient and recyclable catalyst for Suzuki reaction

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Abstract

Palladium cation embedded cellulose acetate/poly(vinyl butyral) composite superfine fibers were successfully fabricated by electrospinning. Then, these composite fibers were treated with hydrazine hydrate/NaOH/ethanol solution to regenerate cellulose from cellulose acetate and poly(vinyl alcohol) from poly(vinyl butyral). Meanwhile, the Pd2+ cations were reduced to Pd0 nanoparticles, which were evenly dispersed inside the fibers. The catalytic performance of these embedded Pd0 nanoparticles were evaluated by Suzuki reaction. The catalysis results show that this novel fibrous catalyst was highly active to catalyze the Suzuki reaction of aromatic iodides and bromides with yields over 90%. Moreover, this fibrous palladium catalyst could be readily recovered and reused for 15 times with little loss of initial catalytic activity. The high catalytic activity can be ascribed to the superfine diameter of fibers while the excellent recyclability can be attributed to the embedment of active palladium species inside the fibers. Therefore, we have developed a facile method to prepare highly active and stable cellulose supported palladium fibrous catalysts.

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Acknowledgments

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Funding

National Natural Science Foundation of China (Nos. 12075154 and 11975157).

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Authors and Affiliations

  1. Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, 312000, Zhejiang Province, People’s Republic of China

    Yaqing Liu, Xi Zhang, Xudong Huang, Linjun Shao & Chenze Qi

  2. School of Medicine, Shaoxing University, Shaoxing, 312000, Zhejiang Province, People’s Republic of China

    Guiying Xing

  3. School of Pharmacy, Jiamusi University, Jiamusi, 154007, Heilongjiang, People’s Republic of China

    Chenze Qi, Shujing Zhou & Jinjing Li

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  1. Yaqing Liu
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  2. Xi Zhang
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  3. Xudong Huang
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  4. Linjun Shao
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  5. Guiying Xing
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  6. Chenze Qi
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Contributions

YL, XZ, XH: Investigation. LS, GX: Conceptualization; investigation; writing. CQ: Funding acquisition; supervision. SZ: Resources; writing. JL: Writing, review.

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Correspondence to Linjun Shao or Guiying Xing.

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1H NMR data of the Suzuki coupling products

1H NMR data of the Suzuki coupling products

Biphenyl: 1 H NMR (400 MHz, CDCl3) δ 7.50–7.42 (m, 4 H), 7.29 (t, J = 7.6 Hz, 4 H), 7.20 (t, J = 7.3 Hz, 2 H).

2-Fluoro-1,1’-biphenyl: 1 H NMR (400 MHz, CDCl3) δ 7.60–7.48 (m, 2 H), 7.43–7.17 (m, 5 H), 7.17–7.03 (m, 2 H).

4-Fluoro-1,1’-biphenyl: 1 H NMR (400 MHz, CDCl3) δ 7.39 (ddd, J = 7.1, 5.1, 2.6 Hz, 3 H), 7.14 (ddd, J = 8.2, 7.0, 4.5 Hz, 6 H).

2-Bromo-1,1’-biphenyl: 1 H NMR (400 MHz, CDCl3) δ 7.59–7.48 (m, 4 H), 7.47–7.31 (m, 5 H).

4-Chloro-1,1’-biphenyl: 1 H NMR (400 MHz, CDCl3) δ 7.54–7.45 (m, 4 H), 7.44–7.29 (m, 5 H).

2-methyl-1,1’-biphenyl: 1 H NMR (400 MHz, CDCl3) δ 7.47–7.42 (m, 2 H), 7.41–7.34 (m, 3 H), 7.33–7.25 (m, 4 H), 2.31 (s, 3 H).

3-methyl-1,1’-biphenyl: 1 H NMR (400 MHz, CDCl3) δ 7.59–7.52 (m, 2 H), 7.42–7.25 (m, 6 H), 7.12 (d, J = 7.5 Hz, 1 H), 2.38 (s, 3 H).

4-methyl-1,1’-biphenyl: 1 H NMR (400 MHz, CDCl3) δ 7.58 (dd, J = 7.4, 6.1 Hz, 2 H), 7.51–7.37 (m, 4 H), 7.34–7.20 (m, 3 H), 2.38 (s, 3 H).

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Liu, Y., Zhang, X., Huang, X. et al. Regenerated cellulose supported palladium composite superfine fibers as an efficient and recyclable catalyst for Suzuki reaction. Cellulose 30, 10243–10255 (2023). https://doi.org/10.1007/s10570-023-05502-3

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