화학공학소재연구정보센터
Journal of Industrial and Engineering Chemistry, Vol.75, 253-261, July, 2019
Synthesis of novel and room temperature-operable palladium complexes on graphene oxide: An efficient recyclable catalyst for Suzuki-Miyaura coupling reactions
E-mail:
Novel palladium complexes composed of palladium and a conjugated ligand (imine-aldehyde) were immobilized on graphene oxide. The developed catalyst was characterized by XPS, and TEM. The novel catalyst was proven to be highly efficient for the Suzuki-Miyaura coupling reaction of aryl halides (Br, Cl) with arylboronic acids under mild conditions with a low amount of catalyst (0.1 mol%). In particular, excellent yields could be also obtained at room temperature within 1 h for monosubstituted aryl bromide coupling. Furthermore, the novel catalyst could be reused at least ten times without significant loss of its catalytic activities.
  1. Seechurn CCCJ, Kitching MO, Colacot TJ, Snieckus V, Angew. Chem.-Int. Edit., 51, 5062 (2012)
  2. Lee JY, Ghosh D, Lee JY, Wu SS, Hu CH, Liu SD, Lee HM, Organometallics, 33, 6481 (2014)
  3. Lee DH, Jin MJ, Org. Lett., 13, 252 (2011)
  4. Welch CJ, Albaneze-Walker J, Leonard WR, Biba M, DaSilva J, Henderson D, Laing B, Mathre DJ, Spencer S, Bu XD, Wang TB, Org. Process Res. Dev., 9, 198 (2005)
  5. Astruc D, Inorg. Chem., 46(6), 1884 (2007)
  6. Xue ZQ, Huang PP, Li TS, Qin PX, Xiao D, Liu MH, Chen PL, Wu YJ, Nanoscale, 9, 781 (2017)
  7. Yuan DZ, Chen L, Yuan LG, Liao SJ, Yang MM, Zhang QH, Chem. Eng. J., 287, 241 (2016)
  8. Giacalone F, Campisciano V, Calabrese C, Parola VL, Syrgiannis Z, Prato M, Gruttadauria M, ACS Nano, 10, 4627 (2016)
  9. Jawale DV, Gravel E, Boudet C, Shah N, Geertsen V, Li HY, Namboothiri INN, Doris E, Catal. Sci. Technol., 5, 2388 (2015)
  10. Song HQ, Zhu Q, Zheng XJ, Chen XG, J. Mater. Chem. A, 3, 10368 (2015)
  11. Baran T, Sargin I, Kaya M, Mentes A, Ceter T, J. Colloid Interface Sci., 486, 194 (2017)
  12. Yan JM, Li SJ, Yi SS, Wulan BR , Zheng WT, Jiang Q, Adv. Mater., 30, 170303 (2018)
  13. Li SJ, Ping Y, Yan JM, Wang HL, Wu M, Jiang Q, J. Mater. Chem. A, 3, 14535 (2015)
  14. Li SJ, Bao D, Shi MM, Wulan BR, Yan JM, Jiang Q, Adv. Mater., 29, 170000 (2017)
  15. Chen XM, Wu GH, Chen JM, Chen X, Xie ZX, Wang XR, J. Am. Chem. Soc., 133(11), 3693 (2011)
  16. Fan XB, Zhang GL, Zhang FB, Chem. Soc. Rev., 44, 3023 (2015)
  17. Julkapli NM, Bagheri S, Int. J. Hydrog. Energy, 40(2), 948 (2015)
  18. Sun ZM, Chen JB, Tu T, Green Chem., 19, 789 (2017)
  19. Karimi B, Akhavan PF, Inorg. Chem., 50(13), 6063 (2011)
  20. Valente C, Calimsiz S, Hoi KH, Mallik D, Sayah M, Organ MG, Angew. Chem.-Int. Edit., 51, 3314 (2012)
  21. Kantam ML, Srinivas P, Yadav J, Likhar PR, Bhargava SJ, Org. Chem., 74, 4882 (2009)
  22. Huang R, Shaughnessy KH, Organometallics, 25, 4105 (2006)
  23. Liu QG, Yang XF, Huang YQ, Xu ST, Su X, Pan XL, Xu JM, Wang AQ, Liang CH, Wang XK, Zhang T, Energy Environ. Sci., 8, 3204 (2015)
  24. Song FZ, Zhu QL, Tsumori N, Xu Q, ACS catal., 5, 5141 (2015)
  25. Delaude L, Hans M, Chowdhury S, Org. Synth., 7, 77 (2010)
  26. Xiao LH, Zheng X, Zhao TY, Sun LY, Liu FQ, Gao G, Dong A, Colloid Polym. Sci., 291, 2359 (2013)
  27. Fu YS, Zhu JW, Hu C, Wu XD, Wang X, Nanoscale, 6, 12555 (2014)
  28. Ganguly A, Sharma S, Papakonstantinou P, Hamilton J, J. Phys. Chem. C, 115, 17009 (2011)
  29. Zhao QS, Zhu YZ, Sun Z, Li Y, Zhang GL, Zhang FB, Fan XB, J. Mater. Chem. A, 3, 2609 (2015)
  30. Johra FT, Lee JW, Jung WG, J. Ind. Eng. Chem., 20(5), 2883 (2014)
  31. Shen DK, Chen L, Yang JP, Zhang RY, Wei Y, Li XM, Li W, Sun ZK, Zhu HW, Abdullah AM, Al-Enizi A, Elzatahry AA, Zhang F, Zhao DY, ACS Appl. Mater. Interfaces, 7, 17450 (2015)
  32. Bivona LA, Giacalone F, Vaccaro L, Aprile C, Gruttadauria M, ChemCatChem, 7, 2526 (2015)
  33. Xu SJ, Song KP, Li T, Tan B, J. Mater. Chem. A, 3, 1272 (2015)
  34. Bahadori M, Tangestaninejad S, Moghadam M, Mirkhani V, Mechler A, Mohammadpoor-Baltork I, Zadehahmadi F, Microporous Mesoporous Mater., 253, 102 (2017)
  35. Zhou H, Wu CG, Wu QL, Guo BX, Liu WT, Li GH, Su Q, Mu Y, Polym. Chem., 8, 1488 (2017)
  36. Mohammadinezhad A, Akhlaghinia B, Green Chem., 19, 5625 (2017)
  37. Deng GY, Wang ZG, Macromol. Rapid Commun., 39, 170061 (2018)
  38. Zhu W, Wang X, Li T, Shen R, Hao SJ, Li YX, Wang QQ, Liu ZJ, Gu ZG, Polym. Chem., 9, 1430 (2018)
  39. Ju PY, Wu SJ, Su Q, Li XD, Li GH, Wu QL, J. Mater. Chem. A, 7, 1660 (2019)