Citation: Cao Shasha, Tan Jinqiang, Wu Chonggang. Catalytic Properties of Supported Pd Catalysts for the Heck Cross-Coupling Reactions[J]. Chemistry, ;2019, 82(8): 684-695. shu

Catalytic Properties of Supported Pd Catalysts for the Heck Cross-Coupling Reactions

Hubei Provincial Key Laboratory of Green Materials for Light Industry, Collaborative Innovation Center of Green Light-weight Materials and Processing, and School of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068

Corresponding author: Wu Chonggang, cgwu@mail.hbut.edu.cn
Received Date: 12 December 2018
Accepted Date: 20 May 2019

Figures(10)

Owing to their high catalytic activity as well as stereoselectivity, Pd catalysts have been widely applied to the Heck cross-coupling reactions usually according to a catalytic mechanism comprising four sequential steps of oxidative addition of Pd(0), addition, β-H elimination, and reductive elimination. For ceramic, organic polymer, and organic-inorganic composite supported Pd catalysts, a rise in the Pd concentration increases its catalytic surface area; an enhancement of the Pd-support adsorption, a decrease in the size and an increase in the surface structure of the support raise the Pd degree of dispersion, an increase in the unsaturated coordination sites (UCSs) of the Pd accelerates its coordination with the reaction substrate to form an intermediate; an improvement in the degree of swelling of the support by the solvent expands the effective contact area between the Pd and the reaction substrate; and increases in the basicity and dosage of the base facilitate the Pd regeneration in the catalytic cycle, all of which enhance the catalytic activity of the Pd. Nevertheless, as the reaction temperature is raised steadily, the Pd catalytic activity usually increases first, going through a maximum at an optimum temperature, and then turns to decrease due to too significant thermal aggregation of the Pd. It has been one of the trends in the Heck reactions to develop supported Pd catalysts of clear catalytic mechanism, high catalytic activity, strong stereoselectivity, and satisfactory reusability.
- The Heck reaction,
- Supported Pd catalyst,
- Catalytic mechanism,
- Catalytic activity,
- Reusability
1. [1]
2. [2]
  N Miyaura, K Yamada, A Suzuki. Tetrahed. Lett., 1979, 20(36):3437~3440.
3. [3]
  N Miyaura, A Suzuki. Chem. Commun., 1979, (19):866~867.
4. [4]
  R F Heck, D S Breslow. J. Am. Chem. Soc., 1961, 83(19):4023~4027.
5. [5]
  R F Heck, J P Nolley. J. Org. Chem., 1972, 37(14):2320~2322.
6. [6]
  K Sonogashira, Y Tohda, N Hagihara. Tetrahed. Lett., 1975, 16(50):4467~4470.
7. [7]
  S Takahashi, Y Kuroyama, K Sonogashira et al. Synthesis, 1980, 1980(8):627~630.
8. [8]
  K Tamao, K Sumitani, M Kumada. J. Am. Chem. Soc., 1972, 94(12):4374~4376.
9. [9]
  T Hayashi, M Konishi, M Kumada. Tetrahed. Lett., 1979, 20(21):1871~1874.
10. [10]
  S Baba, E Negishi. J. Am. Chem. Soc., 1976, 98(21):6729~6731.
11. [11]
  A O King, E Negishi, F J Villani Jr. et al. J. Org. Chem., 1978, 43(2):358~360.
12. [12]
  D Milstein, J K Stille. J. Am. Chem. Soc., 1978, 100(11):3636~3638.
13. [13]
  T Hiyama, Y Hatanaka. Pure Appl. Chem., 1994, 66(7):1471~1478.
14. [14]
  K Gouda, E Hagiwara, Y Hatanaka et al. J. Org. Chem., 1996, 61(21):7232~7233.
15. [15]
16. [16]
  R F Heck. J. Am. Chem. Soc., 1968, 90(20):5518~5526.
17. [17]
  T Mizoroki, K Mori, A Ozaki. Bull. Chem. Soc. Jpn., 1971, 44(2):581.
18. [18]
  A Schoenberg, I Bartoletti, R F Heck. J. Org. Chem., 1974, 39(23):3318~3326.
19. [19]
  A Schoenberg, R F Heck. J. Am. Chem. Soc., 1974, 96(25):7761~7764.
20. [20]
  R P Hsung, J R Babcock, C E D Chidsey et al. Tetrahed. Lett., 1995, 36(26):4525~4528.
21. [21]
  K Sonogashira. J. Organomet. Chem., 2002, 653(1):46~49.
22. [22]
  V Caló, A Nacci, A Monopoli et al. J. Org. Chem., 2003, 68(7):2929~2933.
23. [23]
  H Zheng, Y Zhu, Y Shi. Angew. Chem. Int. Ed., 2014, 53(42):11280~11284.
24. [24]
  E David, J Lejeune, S Pellet-Rostaing et al. Tetrahed. Lett., 2008, 49(11):1860~1864.
25. [25]
  C Torborg, M Beller. Adv. Synth. Catal., 2009, 351(18):3027~3043.
26. [26]
  J G de Vries. Can. J. Chem., 2001, 79(5-6):1086~1092.
27. [27]
28. [28]
  M Ohff, A Ohff, M E van der Boom et al. J. Am. Chem. Soc., 1997, 119(48):11687~11688.
29. [29]
  A F Littke, G C Fu. J. Org. Chem., 1999, 64(1):10~11.
30. [30]
  M Feuerstein, H Doucet, M Santelli. J. Org. Chem., 2001, 66(17):5923~5925.
31. [31]
  J Hu, Y Lu, Y Li et al. Chem. Commun., 2013, 49(82):9425~9427.
32. [32]
  C S Consorti, M L Zanini, S Leal et al. Org. Lett., 2003, 5(7):983~986.
33. [33]
  T Mino, Y Shirae, Y Sasai et al. J. Org. Chem., 2006, 71(18):6834~6839.
34. [34]
  T Kawano, T Shinomaru, I Ueda. Org. Lett., 2002, 4(15):2545~2547.
35. [35]
  A S Gruber, D Zim, G Ebeling et al. Org. Lett., 2000, 2(9):1287~1290.
36. [36]
  W A Herrmann, C P Reisinger, M Spiegler. J. Organomet. Chem., 1998, 557(1):93~96.
37. [37]
  K Selvakumar, A Zapf, M Beller. Org. Lett., 2002, 4(18):3031~3033.
38. [38]
  B Karimi, D Enders. Org. Lett., 2006, 8(6):1237~1240.
39. [39]
  A B Dounay, L E Overman. Chem. Rev., 2003, 103(8):2945~2964.
40. [40]
  A Sundermann, O Uzan, J M Martin. Chem. Eur. J., 2001, 7(8):1703~1711.
41. [41]
  H Hagiwara, Y Shimizu, T Hoshi et al. Tetrahed. Lett., 2001, 42(26):4349~4351.
42. [42]
43. [43]
44. [44]
  P Serp, M Corrias, P Kalck. Appl. Catal. A, 2003, 253(2):337~358.
45. [45]
46. [46]
  L Wang, L Zhu, N Bing, et al. J. Phys. Chem. Solids, 2017, 107:125~130.
47. [47]
  X W Guo, C H Hao, C Y Wang et al. Catal. Sci. Technol., 2016, 6(21):7738~7743.
48. [48]
  K P de Jong, J W Geus. Catal. Rev., 2000, 42(4):481~510.
49. [49]
  J Zhu, J Zhou, T Zhao et al. Appl. Catal. A, 2009, 352(1):243~250.
50. [50]
  S J Guo, J Bai, H O Liang et al. Chin. Chem. Lett., 2016, 27(3):459~463.
51. [51]
  P Wang, G Zhang, H Jiao et al. Appl. Catal. A, 2015, 489:188~192.
52. [52]
  M Tanhaei, A Mahjoub, R Nejat. Catal. Lett., 2018, 148(11):1549~1561.
53. [53]
  R S Varma. Tetrahedron, 2002, 58(7):1235~1255.
54. [54]
  B M Choudary, R M Sarma, K K Rao. Tetrahedron, 1992, 48(4):719~726.
55. [55]
56. [56]
57. [57]
  C P Mehnert, D W Weaver, J Y Ying. J. Am. Chem. Soc., 1998, 120(47):12289~12296.
58. [58]
59. [59]
  X Ma, Y Zhou, J Zhang et al. Green Chem., 2008, 10(1):59~66.
60. [60]
  L Djakovitch, K Koehler. J. Am. Chem. Soc., 2001, 123(25):5990~5999.
61. [61]
62. [62]
  P D Stevens, G Li, J Fan et al. Chem. Commun., 2005, (35):4435~4437.
63. [63]
  J Yang, D Wang, W Liu et al. Green Chem., 2013, 15(12):3429~3437.
64. [64]
  M Ma, Q Zhang, D Yin et al. Catal. Commun., 2012, 17:168~172.
65. [65]
  A S Singh, U B Patil, J M Nagarkar. Catal. Commun., 2013, 35:11~16.
66. [66]
  S S Soni, D A Kotadia. Catal. Sci. Technol., 2014, 4(2):510~515.
67. [67]
  A Ghorbani-Choghamarani, B Tahmasbi, P Moradi. RSC Adv., 2016, 6(49):43205~43216.
68. [68]
  M Wagner, K Köhler, L Djakovitch et al. Top. Catal., 2000, 13(3):319~326.
69. [69]
  M Benaglia, A Puglisi, F Cozzi. Chem. Rev., 2003, 103(9):3401~3430.
70. [70]
71. [71]
  C Wu, X Peng, L Zhong et al. RSC Adv., 2016, 6(38):32202~32211.
72. [72]
73. [73]
  S Fujita, T Yoshida, B M Bhanage et al. J. Mol. Catal. A, 2002, 188(1~2):37~43.
74. [74]
75. [75]
76. [76]
  V Calò, A Nacci, A Monopoli et al. Organometallics, 2004, 23(22):5154~5158.
77. [77]
78. [78]
  A Khazaei, S Rahmati, Z Hekmatian et al. J. Mol. Catal. A:Chem., 2013, 372:160~166.
79. [79]
  D Astruc, F Chardac. Chem. Rev., 2001, 101(9):2991~3024.
80. [80]
  E H Rahim, F S Kamounah, J Frederiksen et al. Nano Lett., 2001, 1(9):499~501.
81. [81]
  H Alper, P Arya, S C Bourque et al. Can. J. Chem., 2000, 78(6):920~924.
82. [82]
83. [83]
  K Qiao, R Sugimura, Q Bao et al. Catal. Commun., 2008, 9(15):2470~2474.
84. [84]
85. [85]
  W K Oh, S Kim, O Kwon et al. J. Nanosci. Nanotechnol., 2011, 11(5):4254~4260.
86. [86]
  L Yu, Y Huang, Z Wei et al. J. Org. Chem., 2015, 80(17):8677~8683.
87. [87]
  B Karimi, M R Marefat, M Hasannia et al. ChemCatChem., 2016, 8(15):2508~2515.
88. [88]
  S Klingelhöfer, W Heitz, A Greiner et al. J. Am. Chem. Soc., 1997, 119(42):10116~10120.
89. [89]
  N Arsalani, A Akbari, M Amini et al. Catal. Lett., 2017, 147(4):1086~1094.
90. [90]
  N Yuan, V Pascanu, Z Huang et al. J. Am. Chem. Soc., 2018, 140(26):8206~8217.
91. [91]
  A Nuri, N Vucetic, J H Smått et al. Catal. Lett., 2019, 149(7):1941~1951.
92. [92]
  S Ghasemi, S Karim. Colloid Polym. Sci., 2018, 296(8):1323~1332.
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