Citation: Li Hengchao, Zhao Ling, Liu Yan, Zhang Xia, Li Wangbing, Jing Linhai, Huang Jin, Wang Wei. An Efficient Palladium Nanoparticles Catalytic System for Suzuki Coupling Reactions[J]. Chinese Journal of Organic Chemistry, ;2019, 39(11): 3207-3214. doi: 10.6023/cjoc201904069 shu

An Efficient Palladium Nanoparticles Catalytic System for Suzuki Coupling Reactions

  • Corresponding author: Huang Jin, huahuanhuangjin@163.com Wang Wei, wangwei1987@cwnu.edu.cn
  • Received Date: 27 April 2019
    Revised Date: 5 June 2019
    Available Online: 2 November 2019

    Fund Project: Project supported by the National Natural Science Foundation of China (No. 21602144), the Sichuan Science and Technology Program (No. 2018JY0485) and the Fundamental Research Funds of China West Normal University (No. 17E049)the National Natural Science Foundation of China 21602144the Fundamental Research Funds of China West Normal University 17E049the Sichuan Science and Technology Program 2018JY0485

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  • A simple and highly efficient palladium nanoparticles catalytic system was applied in Suzuki coupling reaction. This system could catalyze a variety of aryl halide and arylboronic acid substrates with a wide range of functional groups. A high turnover number of 90000 was obtained with the catalyst loading as low as 0.001 mol%. This catalyst system exhibited good stability and longevity.
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    1. [1]

      Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.  doi: 10.1021/cr00039a007

    2. [2]

      Suzuki, A. Chem. Commun. 2005, 4759.
       

    3. [3]

      Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722.  doi: 10.1002/anie.201101379

    4. [4]

      Capdeville, R.; Buchdunger, E.; Zimmermann, J.; Matter, A. Nat. Rev. Drug Discovery 2002, 1, 493.  doi: 10.1038/nrd839

    5. [5]

      Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651.  doi: 10.1021/cr0505268

    6. [6]

      Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177.  doi: 10.1021/cr100346g

    7. [7]

      Fihri, A.; Bouhrara, M.; Nekoueishahraki, B.; Basset, J.-M.; Polshettiwar, V. Chem. Soc. Rev. 2011, 40, 5181.  doi: 10.1039/c1cs15079k

    8. [8]

      (a) Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417.
      (b) Stockton, K. P.; Merritt, C. J.; Sumby, C. J.; Greatrex, B. W. Eur. J. Org. Chem. 2015, 6999.
      (c) Li, J.-X.; Yang, S.-R.; Wu, W.-Q.; Jiang, H.-F. Eur. J. Org. Chem. 2018, 1284.

    9. [9]

      Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095.

    10. [10]

      Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153.  doi: 10.1002/1521-3773(20001117)39:22<4153::AID-ANIE4153>3.0.CO;2-T

    11. [11]

      Yuan, D.; Huynh, H. V. Organometallics 2010, 29, 6020.  doi: 10.1021/om1008023

    12. [12]

      Bianchini, C.; Lee, H. M.; Meli, A.; Oberhauser, W.; Vizza, F.; Brüggeller, P.; Rainer, H. B.; Langes, C. Chem. Commun. 2000, 777.

    13. [13]

      Nair, P.; Anderson, G. K.; Rath, N. P. Organometallics 2003, 22, 1494.  doi: 10.1021/om0209069

    14. [14]

      Imamoto, T.; Yashio, K.; Crépy, K. V. L.; Katagiri, K.; Takahashi, H.; Kouchi, M.; Gridnev, I. D. Organometallics 2006, 25, 908.  doi: 10.1021/om050759p

    15. [15]

      Field, L. D.; Messerle, B. A.; Smernik, R. J.; Hambley, T. W.; Turner, P. Inorg. Chem. 1997, 36, 2884.  doi: 10.1021/ic970030b

    16. [16]

      (a) Laurenti, D.; Feuerstein, M.; Pèpe, G.; Doucet, H.; Santelli, M. J. Org. Chem. 2001, 66, 1633.
      (b) Feuerstein, M.; Laurenti, D.; Bougeant, C.; Doucet, H.; Santelli, M. Chem. Commun. 2001, 325.
      (c) Feuerstein, M.; Doucet, H.; Santelli, M. Synlett 2001, 9, 1458.
      (d) Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2001, 42, 6667.
      (e) Feuerstein, M.; Doucet, H.; Santelli, M. J. Organomet. Chem. 2003, 687, 327.

    17. [17]

      Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P.; Doucet, H.; Santelli, M.; Donnadieu, B. Organometallics 2003, 22, 4490.  doi: 10.1021/om0302948

    18. [18]

      Zaborova, E.; Deschamp, J.; Guieu, S.; Bleriot, Y.; Poli, G.; Menand, M.; Madec, D.; Prestat, G.; Sollogoub, M. Chem. Commun. 2011, 47, 9206.  doi: 10.1039/c1cc12241j

    19. [19]

      (a) Wang, K.; Yi, T.; Yu, X.-J.; Zheng, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Appl. Organomet. Chem. 2012, 26, 342.
      (b) Wang, K.; Fu, Q.; Zhou, R.; Zheng, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Appl. Organomet. Chem. 2013, 27, 232.
      (c) Wang, K.; Wang, W.; Luo, H.; Zheng, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Catal. Lett. 2013, 143, 1214.
      (d) Guo, F.-C.; Zhou, R.; Jiang, Z.-J.; Wang, W.; Zheng, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Catal. Commun. 2015, 66, 87.

    20. [20]

    21. [21]

    22. [22]

      Arumugam, V.; Kaminsky, W.; Bhuvanesh, N. S. P.; Nallasamy, D. RSC Adv. 2015, 5, 59428.  doi: 10.1039/C5RA10973F

    23. [23]

      Lysén, M.; Köhler, K. Synthesis 2006, 4, 692.
       

    24. [24]

      Jansa, J.; Jambor, R. Appl. Organomet. Chem. 2016, 30, 1036.  doi: 10.1002/aoc.3539

    25. [25]

      Ahmed, J.; Chakraborty, S.; Jose, A.; Mandal, S. K. J. Am. Chem. Soc. 2018, 140, 8330.  doi: 10.1021/jacs.8b04786

    26. [26]

      Klein, M.; Voigtmann, U.; Haack, T.; Erdinger, L.; Boche, G. Mutat. Res. 2000, 467, 55.  doi: 10.1016/S1383-5718(00)00012-7

    27. [27]

      Macé, Y.; Raymondeau, B.; Pradet, C.; Blazejewski, J. C.; Magnier, E. Eur. J. Org. Chem. 2009, 1390.

    28. [28]

      Ernst, J. B.; Rakers, L.; Glorius, F. Synthesis 2017, 49, 260.

    29. [29]

      Duan, X.-Y.; Li, P.-B.; Zhu, G.-R.; Fu, C.-L.; Chen, Q.; Huang, X.; Ma, S.-M. Org. Chem. Front. 2018, 5, 3319.  doi: 10.1039/C8QO00781K

    30. [30]

      Chiu, C. C.; Chiu, H. T.; Lee, D. S.; Lu, T. J. RSC Adv. 2018, 8, 26407.  doi: 10.1039/C8RA04094J

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