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Progress in Chemistry 2023, Vol. 35 Issue (9): 1369-1388 DOI: 10.7536/PC230115 Previous Articles   Next Articles

• Review •

Design, Synthesis and Application of Magnetic Nanoparticle Catalytic Materials Based on Multientate Palladium Compounds

Yunhua Ma, Han Shao, Tenglong Lin, Qinyue Deng()   

  1. College of Materials and Chemistry, University of Shanghai for Science and Technology, Shanghai, 200093, China
  • Received: Revised: Online: Published:
  • Contact: *e-mail: dqy1991@usst.edu.cn
  • Supported by:
    The Shanghai Young Teachers Training and Support Program(slg20035)
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Catalyst loading is one of the effective strategies for green catalysis. Palladium (Pd) catalysts supported by magnetic nanoparticles (MNPs) have been widely studied and used in organic synthesis due to their good dispersibility, high catalytic activity, rapid separation under the action of an external magnetic field, and efficient recovery. The MNPs-supported polydentate Pd compound catalyst (MNPs@L-Pd) shows better catalytic activity and stability than the MNPs-supported Pd nanoparticle catalyst (MNPs@PdNP). This is mainly because the introduction of the modified ligand in MNPs@L-Pd can regulate the electronic effect and steric hindrance of the catalyst metal center to achieve the regulation of its activity, on the other hand, it makes the stable chemical bond between the catalyst metal center and the magnetic material to achieve the regulation of stability. This paper mainly focuses on MNPs@L-Pd, the preparation of MNPs@L-Pd based on different ligands and coordination methods and its application in C-X(Cl, Br, I) activation reaction in the past 10 years are reviewed from the aspects of catalyst stability and activity, and the prospect of these reactions are also presented.

Contents

1 Introduction

2 Palladium-catalyzed system based on bidentate coordination mode

2.1 N-Pd-N coordination bond catalytic system

2.2 O-Pd-N coordination bond catalytic system

2.3 P-Pd-P coordination bond catalytic system

2.4 S-Pd-N coordination bond catalytic system

2.5 Se-Pd-N coordination bond catalytic system

3 Palladium-catalyzed system based on tridentate coordination mode

4 Palladium-catalyzed system based on tetradecentate coordination mode

5 Palladium-catalyzed system based on multidentate coordination mode

6 Palladium-catalyzed system based on Pd-C covalent bonds

7 Conclusion and outlook

Key words: magnetic nanoparticle, palladium complex, supported catalyst, organic synthesis reaction
Fig.1 Schematic diagram of the coordination mode of the dominant fragment of the catalyst
Scheme 1 Synthesis of MNP-1 and its application in Suzuki coupling reaction[19]
Scheme 2 Synthesis of MNP-2 and its application in Suzuki coupling reaction[20]
Scheme 3 Synthesis of MNP-3 and its application in Suzuki coupling reaction[21]
Scheme 4 Synthesis of MNP-4 and its application in Suzuki coupling reaction[22]
Scheme 5 Synthesis of MNP-5 and MNP-6 and their application in Heck coupling reaction[23,24]
Scheme 6 Synthesis of MNP-7 and its application in cross-coupling reaction[25]
Scheme 7 Synthesis of MNP-8 and its application in cross-coupling of C-S and C-Se[26]
Scheme 8 Synthesis of MNP-9 and its application in cross-coupling and cyanidation reactions[27]
Scheme 9 Synthesis of MNP-10 and its application in Heck and Suzuki cross-coupling reactions[29]
Scheme 10 Synthesis of MNP-11 and its application in Suzuki cross-coupling reactions[30]
Scheme 11 Synthesis of MNP-12 and its application in C-C cross-coupling reactions[31]
Scheme 12 Synthesis of MNP-13 and its application in C-C cross-coupling reactions[32]
Scheme 13 Synthesis of MNP-14 and its application in C-C cross-coupling reactions[33]
Scheme 14 Synthesis of MNP-15 and its application in Heck coupling reactions[34]
Scheme 15 Synthesis of MNP-16 and its application in Heck coupling reactions[37]
Scheme 16 Synthesis of MNP-17 and its application in Buchwald-Hartwig amination[38]
Scheme 17 Synthesis of MNP-18 and its application in C-C coupling reactions[39]
Scheme 18 Synthesis of MNP-19 and its application in Heck coupling reactions[40]
Scheme 19 Synthesis of MNP-20 and its application in Suzuki coupling reactions[41]
Scheme 20 Synthesis of MNP-21 and its application in C-C coupling reactions[42]
Scheme 21 Synthesis of MNP-22 and its application in Sonogashira coupling reactions[43]
Scheme 22 Synthesis of MNP-23 and its application in C-C coupling reactions[44]
Scheme 23 Synthesis of MNP-24 and its application in C-C coupling reactions[45]
Scheme 24 Synthesis of MNP-25 and its application in C-C coupling reactions[46]
Scheme 25 Synthesis of MNP-26 and its application in CO2 cyclocarbonate reaction[48]
Scheme 26 Synthesis of MNP-27 and its application in Suzuki coupling reactions[49]
Scheme 27 Synthesis of MNP-28 and its application in Suzuki coupling reactions[50]
Scheme 28 Synthesis of MNP-29 and its application in C-C coupling reactions[51]
Scheme 29 Synthesis of MNP-30 and its application in C-C coupling reactions[52]
Scheme 30 Schematic representation of the structures of MNP-31 and MNP-32[53]
Scheme 31 Synthesis of MNP-33 and its application in C-C coupling reactions[54]
Scheme 32 Synthesis of MNP-34 and its application in Suzuki coupling reactions[55]
Scheme 33 Synthesis of MNP-35 and MNP-36 and their application in Suzuki coupling reactions[56,57]
Scheme 34 Synthesis of MNP-37 and its application in Suzuki coupling reactions[58]
Scheme 35 Synthesis of MNP-38 and its application in Suzuki coupling reactions[59]
Scheme 36 Synthesis of MNP-39 and its application in C-C coupling reactions[60]
Scheme 37 Synthesis of MNP-40 and its application in C-C coupling reactions[61,62]
Scheme 38 Synthesis of MNP-41 and its application in Suzuki coupling reactions[63]
Table 1 Performance of catalysts supported by different magnetic nanoparticles for Suzuka-Miyaura reaction
Pd catalyst (mol%) Standard conditions Yield(%) Reusability TOF(h-1) ref
MNP-2 (0.14 mol% Pd) K2CO3, EtOH/H2O(1∶1), 80 ℃, 50 min 95% 8 814.28 20a
MNP-3 (0.01 mol% Pd) K2CO3, EtOH/H2O(1∶1), 70 ℃, 30 min 96% 12 19 200 21a
MNP-4 (0.1 mol% Pd) Et3N or Na2CO3, EtOH/H2O(1∶1), 80 ℃,
30 min		 99% 7 1980 22b
MNP-10 (0.009 mol% Pd) K2CO3, EtOH/H2O(1∶1), 75 ℃, 1.0 h 97% 5 10 778 29a
MNP-12 (0.47 mol% Pd) K2CO3, H2O, 60~90 ℃, 20 min 95% 6 612 31a
MNP-13 (0.1 mol% Pd) K2CO3, H2O, 90 ℃, 1.0 h 95% 6 950 32a
MNP-14 (0.09 mol% Pd) K2CO3, H2O, reflux, 1.0 h 93% 6 1033.3 33a
MNP-18 (0.01 mol% Pd) Et3N, H2O, 80 ℃, 45 min 91% 9 12 133.3 39a
MNP-20 (0.04 mol% Pd ) K2CO3, EtOH/H2O(2∶1), 60 ℃, 1.5 h 95% 7 1583.3 41a
MNP-21 (0.5 mol% Pd) Et3N, DMF, 100 ℃, 3 h 92% 10 61.3 42a
MNP-23 (0.3 mol% Pd) K2CO3, NMP, 100 ℃, 2.5 h 88% 8 117 44a
MNP-27 (0.017 mol% Pd) K2CO3, EtOH/H2O(1∶1), 80 ℃, 3.0 h 86% 7 1686.3 49a
MNP-28 (0.34 mol% Pd) K2CO3, EtOH/H2O(2∶1), 60 ℃, 3.0 h 92% 20 6903 50a
MNP-29 (0.825 mol% Pd) K2CO3, NMP, 90 ℃, 1.0 h 88% 6 107 51a
MNP-34 (0.5 mol%) K3PO4, Toluene, 100 ℃, 24.0 h 99% 7 8.25 55c
MNP-35 (0.15 mol% Pd) K2CO3, EtOH/H2O(1∶1), 70 ℃, 1.0 h 95% 5 633.3 56a
MNP-36 (0.15 mol% Pd) K2CO3, EtOH/H2O(1∶1), R.T, 2.0 h 95% 7 316.7 57a
MNP-37 (0.022 mmol% Pd ) Na2CO3, EtOH, 60 ℃, 20 min 95% 5 12 954.5 58a
MNP-38 (0.021 mmol% Pd) NaHCO3, EtOH/H2O(1∶1), 70 ℃, 10 min 98% 13 2940×104 59a
MNP-39 (0.37 mol% Pd ) K2CO3, H2O, 60 ℃, 3.0 h 96% 8 86.5 60a
MNP-40-A (1.5 mol% ) Na2CO3, PEG-400, 80 ℃, 100 min 88% 8 35.2 61a
MNP-40-B (0.83 mol% ) Na2CO3, PEG-400, 80 ℃, 3.0 h 93% 7 37.3 62a
MNP-41 (0.5 mol%) K2CO3, EtOH/H2O(2∶1), 60 ℃, 12.0 h 93% 12 15.5 63d
Table 2 Performance of catalysts supported by different magnetic nanoparticles for Heck reaction
Pd catalyst (mol%) Standard conditions Yield(%) Reusability TOF(h-1) ref
MNP-5 (3.58 mol%) K2CO3, DMF, 100 ℃, 8 h 93% 8 3.25 23a
MNP-6 (1.24 mol% Pd) Et3N, DMSO, 100 ℃, 1.5 h 92% 6 49 24a
MNP-10 (0.009 mol% Pd) Et3N, Solvent-free, 120 ℃, 40 min 96% 5 16000 29b
MNP-12 (0.61mol% Pd) K2CO3, H2O, 80~90 ℃, 50 min 95% 6 187 31c
MNP-13 (0.1 mol% Pd) K2CO3, H2O/DMF(1∶1), reflux, 8.0 h 95% 6 122.5 32a
MNP-14 (0.09 mol% Pd) K2CO3, H2O, reflux, 12 h 96% 6 88.8 33d
MNP-15 (0.71 mol% Pd) Et3N, DMF, TBAB, 120 ℃, 20 min 93% 10 393 34b
MNP-19 (0.15 mol% Pd ) Et3N, DMF, 120 ℃, 45 min 98% 5 871.1 40b
MNP-21 (0.5 mol% Pd) Et3N, DMF, 100 ℃, 0.25 h 98% 10 784 42c
MNP-23 (0.3 mol% Pd) K2CO3, DMF, 110 ℃, 0.75 h 97% 8 430 44c
MNP-24 (0.2 mol% Pd) K2CO3, H2O/DMF(2∶1), 90 ℃, 0.5 h 95% 8 950 45c
MNP-25 (0.08 mol% Pd) NaOAc, H2O, R.T., 1.0 h 98% 10 1225 46a
MNP-29 (0.99 mol% Pd ) K2CO3, NMP, 110 ℃, 0.5 h 96% 6 194 51c
MNP-30 (0.0435 mol% Pd) NaOAc, H2O, R.T., 1.0 h 95% 10 2183.9 52a
MNP-36 (1.0 mol% Pd) Na3PO4·12H2O, MeCN, 80 ℃, 4.0 h 96% 7 24 57e
MNP-40-A(2.27 mol% ) Na2CO3, PEG-400, 120 ℃, 80 min 96% 7 31.7 61c
MNP-40-B(1.46 mol% ) Na2CO3, PEG-400, 120 ℃, 1.0 h 98% 7 67.1 62c
Table 3 Performance of catalysts supported by different magnetic nanoparticles for other C-C coupling reactions
Pd catalyst (mol%) Standard conditions Yield(%) Reusability TOF(h-1) ref
MNP-21(0.5 mol% Pd) Et3N, DMF, 100 ℃, 1.5 h 96% 10 128 42a
MNP-18(0.1 mol% Pd) Et3N, H2O, 80 ℃, 0.5 h 90% 9 1800 42b
MNP-18(0.2 mol% Pd) Et3N, H2O, 80 ℃, 6.0 h 99% 9 82.5 42c
MNP-22 (0.7 mol% Pd) Et3N, DMF, 90 ℃, 0.5 h 94% 6 268.6 43a
MNP-24 (0.2 mol% Pd) K2CO3, H2O/DMF(2∶1), 90 ℃, 1.0 h 96% 8 480 45a
MNP-25 (0.08 mol%) NaOAc, H2O, R.T., 1.0 h 94% 10 1175 46a
MNP-30(0.0435 mol% Pd) NaOAc, H2O, R.T., 1.0 h 95% 10 2184 52a
MNP-39(0.43 mol% Pd ) Piperidine, Solvent-free, 90 ℃, 1.5 h 95% 8 147.3 60a
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