Immobilized Pd nanoparticles on Tris-modified SiO2：Synthesis, characterization, and catalytic activity in Heck cross-coupling reactions

doi:10.1016/S1872-2067(14)60109-1

Abstract

Abstract:

The preparation of supported Pd nanoparticles on Tris (tris(hydroxymethyl)aminomethane)- modified SiO₂ gel and their catalytic application in Heck coupling are investigated. The catalyst was characterized using a combination of X-ray diffraction, transmission electron microscopy, field-emission scanning electron microscopy, and scanning electron microscopy/energy-dispersive X-ray spectroscopy. The supported Pd nanoparticles were found to be a highly active and reusable catalyst for the Heck reaction at a low Pd loading (0.02 mol%) because of stabilization by the Tris moieties. Several reaction parameters, including the type and amount of solvent, base, and temperature, were evaluated. The heterogeneity of the catalytic system was investigated using different approaches, and showed that slight Pd leaching into the reaction solution occurred under the reaction conditions. Despite this metal leaching, the catalyst can be reused seven times without significant loss of its activity.

Key words: Supported palladium nanoparticle, Heterogeneous catalyst, Heck coupling, Carbon-carbon coupling reaction

Abdol R. Hajipour, Ghobad Azizi. Immobilized Pd nanoparticles on Tris-modified SiO₂：Synthesis, characterization, and catalytic activity in Heck cross-coupling reactions[J]. Chinese Journal of Catalysis, 2014, 35(9): 1547-1554.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60109-1

https://www.cjcatal.com/EN/Y2014/V35/I9/1547

References

[1] Turner M, Golovko V B, Vaughan O P H, Abdulkin P, Berenguer- Murcia A, Tikhov M S, Johnson B F G, Lambert R M. Nature, 2008, 454: 981
[2] Astruc D, Lu F, Aranzaes J R. Angew Chem Int Ed, 2005, 44: 7852
[3] Beletskaya I P, Cheprakov A V. Chem Rev, 2000, 100: 3009
[4] de Vries J G. Can J Chem, 2001, 79: 1086
[5] Pirisedigh A, Zarei A, Seyedjamali H, Khazdooz L, Hajipour A R. Monatsh Chem, 2012, 143: 791
[6] Saha M, Pal A K. Tetrahedron Lett, 2011, 52: 4872
[7] Zarei A, Khazdooz L, Pirisedigh A, Hajipour A R, Seyedjamali H, Aghaei H. Tetrahedron Lett, 2011, 52: 4554
[8] Hajipour A R, Rafiee F. J Organomet Chem, 2011, 696: 2669
[9] Hajipour A R, Rafiee F. App Organomet Chem, 2011, 25: 542
[10] Karimi B, Enders D. Org Lett, 2006, 8: 1237
[11] Schönfelder D, Nuyken O, Weberskirch R. J Organomet Chem, 2005, 690: 4648
[12] Gruber-Woelfler H, Radaschitz P F, Feenstra P W, Haas W, Khinast J G. J Catal, 2012, 286: 30
[13] Polshettiwar V, Varma R S. Org Biomol Chem, 2009, 7: 37
[14] Polshettiwar V, Hesemann P, Moreau J J E. Tetrahedron, 2007, 63: 6784
[15] Uozumi Y, Kimura T. Synlett, 2002: 2045
[16] Bakherad M, Keivanloo A, Samangooei S. Chin. J. Catal (催化学报), 2014, 35: 324-328
[17] Chen G F, Wang F, Wang Y H, Zhang X C, Qin H Q, Zou H F, Xu J. Chin J Catal (催化学报), 2014, 35: 540
[18] Feng Y J, Li L, Li Y S, Zhao W R, Gu J L, Shi J L. J Mol Catal A, 2010, 322: 50
[19] Zhang F W, Jin J, Zhong X, Li S W, Niu J R, Li R, Ma J T. Green Chem, 2011, 13: 1238
[20] Yang X, Fei Z F, Zhao D, Ang W H, Li Y D, Dyson P J. Inorg Chem, 2008, 47: 3292
[21] Tao R T, Miao S D, Liu Z M, Xie Y, Han B X, An G M, Ding K L. Green Chem, 2009, 11: 96
[22] Senapati K K, Roy S, Borgohain C, Phukan P. J Mol Catal A, 2012, 352: 128
[23] Proch S, Mei Y, Villanueva J M R, Lu Y, Karpov A, Ballauff M, Kempe R. Adv Synth Catal, 2008, 350: 493
[24] Liu G, Hou M Q, Song J Y, Jiang T, Fan H L, Zhang Z F, Han B X. Green Chem, 2010, 12: 65
[25] Ko S, Jang J. Angew Chem Int Ed, 2006, 45: 7564
[26] Costa N J S, Kiyohara P K, Monteiro A L, Coppel Y, Philippot K, Rossi L M. J Catal, 2010, 276: 382
[27] Corma A, Iborra S, Llabrés i Xamena F X, Montón R, Calvino J J, Prestipino C. J Phys Chem C, 2010, 114: 8828
[28] Cirtiu C M, Dunlop-Briere A F, Moores A. Green Chem, 2011, 13: 288
[29] Boudjahem A-G, Mokrane T, Redjel A, Bettahar M M. C R Chim, 2010, 13: 1433
[30] Yang H Q, Han X J, Li G, Wang Y W. Green Chem, 2009, 11: 1184
[31] Polshettiwar V, Molnár Á. Tetrahedron, 2007, 63: 6949
[32] Richardson J M, Jones C W. J Catal, 2007, 251: 80
[30] Zhao F Y, Shirai M, Ikushima Y, Arai M. J Mol Catal A, 2002, 180: 211

Immobilized Pd nanoparticles on Tris-modified SiO₂：Synthesis, characterization, and catalytic activity in Heck cross-coupling reactions

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

[1]	Yuzhuo Chen, Hao Wang, Bing Lu, Ni Yi, Liang Cao, Yong Wang, Shanjun Mao. Fine-structure sensitive deep learning framework for predicting catalytic properties with high precision [J]. Chinese Journal of Catalysis, 2023, 50(7): 284-296.
[2]	Wanjun Sun, Jiayu Zhu, Meiyu Zhang, Xiangyu Meng, Mengxue Chen, Yu Feng, Xinlong Chen, Yong Ding. Recent advances and perspectives in cobalt-based heterogeneous catalysts for photocatalytic water splitting, CO₂ reduction, and N₂ fixation [J]. Chinese Journal of Catalysis, 2022, 43(9): 2273-2300.
[3]	Ya-Fei Jiang, Jin-Cheng Liu, Cong-Qiao Xu, Jun Li, Hai Xiao. Breaking the scaling relations for efficient N₂-to-NH₃ conversion by a bowl active site design: Insight from LaRuSi and isostructural electrides [J]. Chinese Journal of Catalysis, 2022, 43(8): 2183-2192.
[4]	Xiaoyan Liu, Guojun Lan, Zhenqing Li, Lihua Qian, Jian Liu, Ying Li. Stabilization of heterogeneous hydrogenation catalysts for the aqueous-phase reactions of renewable feedstocks [J]. Chinese Journal of Catalysis, 2021, 42(5): 694-709.
[5]	Wenjuan Yan, Dongpei Zhang, Yu Sun, Ziqi Zhou, Yihang Du, Yiyao Du, Yushan Li, Mengyuan Liu, Yuming Zhang, Jian Shen, Xin Jin. Structural sensitivity of heterogeneous catalysts for sustainable chemical synthesis of gluconic acid from glucose [J]. Chinese Journal of Catalysis, 2020, 41(9): 1320-1336.
[6]	Yan Zhang, Hui Hu, Jia Ju, Qianqian Yan, Vasanthakumar Arumugam, Xuechao Jing, Huaqiang Cai, Yanan Gao. Ionization of a covalent organic framework for catalyzing the cycloaddition reaction between epoxides and carbon dioxide [J]. Chinese Journal of Catalysis, 2020, 41(3): 485-493.
[7]	Zhong-Pan Hu, Dandan Yang, Zheng Wang, Zhong-Yong Yuan. State-of-the-art catalysts for direct dehydrogenation of propane to propylene [J]. Chinese Journal of Catalysis, 2019, 40(9): 1233-1254.
[8]	Zhongzhe Wei, Fangjun Shao, Jianguo Wang. Recent advances in heterogeneous catalytic hydrogenation and dehydrogenation of N-heterocycles [J]. Chinese Journal of Catalysis, 2019, 40(7): 980-1002.
[9]	Pingping Zha, Yunyun Zhan, Daokuan L, Hongyou Cu, Lipeng Zhan. Mesoporous polyoxometalate-based ionic hybrid as a highly effective heterogeneous catalyst for direct hydroxylation of benzene to phenol [J]. Chinese Journal of Catalysis, 2018, 39(2): 334-341.
[10]	Ye Lu, Yoshinori Yamamoto, Abdulrahman I. Almansour, Natarajan Arumugam, Raju Suresh Kumar, Ming Bao. Unsupported nanoporous palladium-catalyzed chemoselective hydrogenation of quinolines:Heterolytic cleavage of H₂ molecule [J]. Chinese Journal of Catalysis, 2018, 39(11): 1746-1752.
[11]	Xiaoming Yan, Xuan Ding, Yu Pan, Xiaowei Xu, Ce Hao, Wenji Zheng, Gaohong He. Quaternary-ammonium-immobilized polystyrenes as efficient and reusable heterogeneous catalysts for synthesis of cyclic carbonate: Effects of linking chains and pendent hydroxyl group [J]. Chinese Journal of Catalysis, 2017, 38(5): 862-871.
[12]	Haipeng Fan, Zhengliang Qi, Dejun Sui, Fei Mao, Rizhi Chen, Jun Huang. Palladium nanoparticles in cross-linked polyaniline as highly efficient catalysts for Suzuki-Miyaura reactions [J]. Chinese Journal of Catalysis, 2017, 38(3): 589-596.
[13]	Mahdi Mirzaee, Bahram Bahramian, Marieh Mirebrahimi. Amine-functionalized boehmite nanoparticle-supported molybdenum and vanadium complexes: Efficient catalysts for epoxidation of alkenes [J]. Chinese Journal of Catalysis, 2016, 37(8): 1263-1274.
[14]	Lanhui Ren, Lianyue Wang, Ying Lü, Guosong Li, Shuang Gao. Direct oxidation of the C_sp₃-H bonds of N-heterocyclic compounds to give the corresponding ketones using a reusable heterogeneous MnO_x-N@C catalyst [J]. Chinese Journal of Catalysis, 2016, 37(8): 1216-1221.
[15]	Yanmei Zhang, Jing Zhang, Miaomiao Tian, Gang Chu, Chunshan Quan. Fabrication of amino-functionalized Fe₃O₄@Cu₃(BTC)₂ for heterogeneous Knoevenagel condensation [J]. Chinese Journal of Catalysis, 2016, 37(3): 420-427.