Preparation and characterization of HypoGel-supported Pd nanocatalysts for Suzuki reaction under mild conditions

Kin Hong Liew Wan Zurina Samad Norazzizi Nordin Poh Lee Loh Joon Ching Juan Mohd Ambar Yarmo Badrul Hisham Yahaya Rahimi M. Yusop

引用本文: Kin Hong Liew, Wan Zurina Samad, Norazzizi Nordin, Poh Lee Loh, Joon Ching Juan, Mohd Ambar Yarmo, Badrul Hisham Yahaya, Rahimi M. Yusop. Preparation and characterization of HypoGel-supported Pd nanocatalysts for Suzuki reaction under mild conditions[J]. 催化学报, 2015, 36(5): 771-777. doi: 10.1016/S1872-2067(14)60282-5 shu
Citation:  Kin Hong Liew, Wan Zurina Samad, Norazzizi Nordin, Poh Lee Loh, Joon Ching Juan, Mohd Ambar Yarmo, Badrul Hisham Yahaya, Rahimi M. Yusop. Preparation and characterization of HypoGel-supported Pd nanocatalysts for Suzuki reaction under mild conditions[J]. Chinese Journal of Catalysis, 2015, 36(5): 771-777. doi: 10.1016/S1872-2067(14)60282-5 shu

Preparation and characterization of HypoGel-supported Pd nanocatalysts for Suzuki reaction under mild conditions

    通讯作者: Rahimi M. Yusop
  • 基金项目:

    This work was supported by the Ministry of Higher Education Malaysia (FRGS/1/2012/ST01/UKM/02/1) (FRGS/1/2012/ST01/UKM/02/1)

    Research Grant from UKM (IP-2014-070 and LAUREATE-2013-002). (IP-2014-070 and LAUREATE-2013-002)

摘要: A new heterogeneous catalyst composed of Pd nanoparticles immobilized within a HypoGel resin has been prepared in the absence of any ligands using an extensive cross-linking method. This newly developed nanocatalyst was characterized by N2 adsorption-desorption, X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray (EDX), Fourier transform infrared spectroscopy and inductively coupled plasma-mass spectrometer (ICP-MS) techniques. TEM and XRD results revealed that the Pd nanoparticles were well dispersed with diameters in the range of 4-12 nm, and an average size of about 8 nm. The cross-linked Pd catalyst demonstrated excellent catalytic activity towards the synthesis of a series of biaryl compounds by the reaction of various aryl halides (e.g., bromides andiodides) with phenylboronic acid in the presence of tetrabutylammonium bromide. ICP-MS analysis indicated that there was only 0.25% weight loss of Pd (0.55 ± 0.02 ppm) from the supported catalyst after the first cycle reaction. Furthermore, the catalyst showed excellent reusability (up to five uses) with consistently high levels of catalytic activity following its recovery by filtration.

English

    1. [1] Miyaura N, Suzuki A. Chem Rev, 1995, 95: 2457[1] Miyaura N, Suzuki A. Chem Rev, 1995, 95: 2457

    2. [2] Suzuki A. J Organomet Chem, 1999, 576: 147[2] Suzuki A. J Organomet Chem, 1999, 576: 147

    3. [3] Xue L Q, Lin Z Y. Chem Soc Rev, 2010, 39: 1692[3] Xue L Q, Lin Z Y. Chem Soc Rev, 2010, 39: 1692

    4. [4] Newman S G, Lautens M. J Am Chem Soc, 2011, 133: 1778[4] Newman S G, Lautens M. J Am Chem Soc, 2011, 133: 1778

    5. [5] Miyaura N, Yanagi T, Suzuki A. Synth Commun, 1981, 11: 513[5] Miyaura N, Yanagi T, Suzuki A. Synth Commun, 1981, 11: 513

    6. [6] Karami K, Ghasemi M, Naeini N H. Catal Commun, 2013, 38: 10[6] Karami K, Ghasemi M, Naeini N H. Catal Commun, 2013, 38: 10

    7. [7] Van der Boom M E, Milstein D. Chem Rev, 2003, 103: 1759[7] Van der Boom M E, Milstein D. Chem Rev, 2003, 103: 1759

    8. [8] Cole-Hamilton D J. Science, 2003, 299: 1702[8] Cole-Hamilton D J. Science, 2003, 299: 1702

    9. [9] Dell'Anna M M, Mali M, Mastrorilli P, Rizzuti A, Ponzoni C, Leonelli C. J Mol Catal A, 2013, 366: 186[9] Dell'Anna M M, Mali M, Mastrorilli P, Rizzuti A, Ponzoni C, Leonelli C. J Mol Catal A, 2013, 366: 186

    10. [10] Li H Q, Han L N, Cooper-White J, Kim I. Green Chem, 2012, 14: 586[10] Li H Q, Han L N, Cooper-White J, Kim I. Green Chem, 2012, 14: 586

    11. [11] Senapati K K, Roy S, Borgohain C, Phukan P. J Mol Catal A, 2012, 352: 128[11] Senapati K K, Roy S, Borgohain C, Phukan P. J Mol Catal A, 2012, 352: 128

    12. [12] Zhu W C, Yang Y, Hu S, Xiang G L, Xu B, Zhuang J, Wang X. Inorg Chem, 2012, 51: 6020[12] Zhu W C, Yang Y, Hu S, Xiang G L, Xu B, Zhuang J, Wang X. Inorg Chem, 2012, 51: 6020

    13. [13] Moussa S, Siamaki A R, Gupton B F, El-Shall M S. ACS Catal, 2012, 2: 145[13] Moussa S, Siamaki A R, Gupton B F, El-Shall M S. ACS Catal, 2012, 2: 145

    14. [14] Coccia F, Tonucci L, d'Alessandro N, D'Ambrosio P, Bressan M. Inorg Chim Acta, 2013, 399: 12[14] Coccia F, Tonucci L, d'Alessandro N, D'Ambrosio P, Bressan M. Inorg Chim Acta, 2013, 399: 12

    15. [15] Park S, Seo J G, Jung J C, Baeck S H, Kim T J, Chung Y M, Oh S H, Song I K. Catal Commun, 2009, 10: 1762[15] Park S, Seo J G, Jung J C, Baeck S H, Kim T J, Chung Y M, Oh S H, Song I K. Catal Commun, 2009, 10: 1762

    16. [16] Akai Y, Yamamoto T, Nagata Y, Ohmura T, Suginome M. J Am Chem Soc, 2012, 134: 11092[16] Akai Y, Yamamoto T, Nagata Y, Ohmura T, Suginome M. J Am Chem Soc, 2012, 134: 11092

    17. [17] Liew K H, Loh P L, Juan J C, Yarmo M A, Yusop R M. Sci World J, 2014: 796196[17] Liew K H, Loh P L, Juan J C, Yarmo M A, Yusop R M. Sci World J, 2014: 796196

    18. [18] Uozumi Y, Nakai Y. Org Lett, 2002, 4: 2997[18] Uozumi Y, Nakai Y. Org Lett, 2002, 4: 2997

    19. [19] Smith C D, Baxendale I R, Lanners S, Hayward J J, Smith S C, Ley S V. Org Biomol Chem, 2007, 5: 1559[19] Smith C D, Baxendale I R, Lanners S, Hayward J J, Smith S C, Ley S V. Org Biomol Chem, 2007, 5: 1559

    20. [20] Bester K, Bukowska A, Bukowski W. Appl Catal A, 2012, 443-444: 181[20] Bester K, Bukowska A, Bukowski W. Appl Catal A, 2012, 443-444: 181

    21. [21] Zhao F Y, Shirai M, Arai M. J Mol Catal A, 2000, 154: 39[21] Zhao F Y, Shirai M, Arai M. J Mol Catal A, 2000, 154: 39

    22. [22] Sin E, Yi S S, Lee Y S. J Mol Catal A, 2010, 315: 99[22] Sin E, Yi S S, Lee Y S. J Mol Catal A, 2010, 315: 99

    23. [23] Liu S Y, Zhou Q Z, Jin Z N, Jiang H J, Jiang X Z. Chin J Catal (刘诗咏, 周其忠, 金正能, 蒋华江, 姜玄珍. 催化学报), 2010, 31: 557[23] Liu S Y, Zhou Q Z, Jin Z N, Jiang H J, Jiang X Z. Chin J Catal (刘诗咏, 周其忠, 金正能, 蒋华江, 姜玄珍. 催化学报), 2010, 31: 557

    24. [24] Phan N T S, Jones C W. J Mol Catal A, 2006, 253: 123[24] Phan N T S, Jones C W. J Mol Catal A, 2006, 253: 123

    25. [25] Ma H C, Bao Z K, Han G B, Yang N N, Xu Y F, Yang Z M, Cao W, Ma Y. Chin J Catal (马恒昌, 包志康, 韩国斌, 杨宁宁, 许玉菲, 杨增明, 曹伟, 马源. 催化学报), 2013, 34: 578[25] Ma H C, Bao Z K, Han G B, Yang N N, Xu Y F, Yang Z M, Cao W, Ma Y. Chin J Catal (马恒昌, 包志康, 韩国斌, 杨宁宁, 许玉菲, 杨增明, 曹伟, 马源. 催化学报), 2013, 34: 578

    26. [26] Ito T, Suda K, Kumamoto T, Nakanishi W, Watanabe T, Ishikawa T, Seki H, Kawahata M, Yamaguchi K, Ogura Y, Suzuki K T. Mol Divers, 2010, 14: 131[26] Ito T, Suda K, Kumamoto T, Nakanishi W, Watanabe T, Ishikawa T, Seki H, Kawahata M, Yamaguchi K, Ogura Y, Suzuki K T. Mol Divers, 2010, 14: 131

    27. [27] Suzuki N, Kishimoto K, Yamazaki K, Kumamoto T, Ishikawa T, Margetić D. Synlett, 2013, 24: 2510[27] Suzuki N, Kishimoto K, Yamazaki K, Kumamoto T, Ishikawa T, Margetić D. Synlett, 2013, 24: 2510

    28. [28] Bagheri M, Beyermann M, Dathe M. Antimicrob Agents Chemother, 2009, 53: 1132[28] Bagheri M, Beyermann M, Dathe M. Antimicrob Agents Chemother, 2009, 53: 1132

    29. [29] Costa F, Carvalho I F, Montelaro R C, Gomes P, Martins M C. Acta Biomater, 2011, 7: 1431[29] Costa F, Carvalho I F, Montelaro R C, Gomes P, Martins M C. Acta Biomater, 2011, 7: 1431

    30. [30] Yusop R M, Unciti-Broceta A, Johansson E M V, Sánchez-Martín R M, Bradley M. Nat Chem, 2011, 3: 239[30] Yusop R M, Unciti-Broceta A, Johansson E M V, Sánchez-Martín R M, Bradley M. Nat Chem, 2011, 3: 239

    31. [31] Cho J K, Najman R, Dean T W, Ichihara O, Muller C, Bradley M. J Am Chem Soc, 2006, 128: 6276[31] Cho J K, Najman R, Dean T W, Ichihara O, Muller C, Bradley M. J Am Chem Soc, 2006, 128: 6276

    32. [32] Unciti-Broceta A, Johansson E M V, Yusop R M, Sánchez-Martín R M, Bradley M. Nat Protoc, 2012, 7: 1207[32] Unciti-Broceta A, Johansson E M V, Yusop R M, Sánchez-Martín R M, Bradley M. Nat Protoc, 2012, 7: 1207

    33. [33] Najman R, Cho J K, Coffey A F, Davies J W, Bradley M. Chem Commun, 2007: 5031[33] Najman R, Cho J K, Coffey A F, Davies J W, Bradley M. Chem Commun, 2007: 5031

    34. [34] Shen C M, Su Y K, Yang H T, Yang T Z, Gao H J. Chem Phys Lett, 2003, 373: 39[34] Shen C M, Su Y K, Yang H T, Yang T Z, Gao H J. Chem Phys Lett, 2003, 373: 39

    35. [35] Socrates G. Infrared and Raman Characteristic Group Frequencies: Tables and Charts. 3rd Ed. London: Wiley, 2004[35] Socrates G. Infrared and Raman Characteristic Group Frequencies: Tables and Charts. 3rd Ed. London: Wiley, 2004

    36. [36] Wu X F, Anbarasan P, Neumann H, Beller M. Angew Chem Int Ed, 2010, 49: 9047[36] Wu X F, Anbarasan P, Neumann H, Beller M. Angew Chem Int Ed, 2010, 49: 9047

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  • 发布日期:  2015-05-20
  • 收稿日期:  2014-12-19
  • 网络出版日期:  2015-01-07
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