Citation:
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.
doi:
10.1016/S1872-2067(14)60109-1
-
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.
-
-
-
[1]
[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]
[2] Astruc D, Lu F, Aranzaes J R. Angew Chem Int Ed, 2005, 44: 7852
-
[3]
[3] Beletskaya I P, Cheprakov A V. Chem Rev, 2000, 100: 3009
-
[4]
[4] de Vries J G. Can J Chem, 2001, 79: 1086
-
[5]
[5] Pirisedigh A, Zarei A, Seyedjamali H, Khazdooz L, Hajipour A R. Monatsh Chem, 2012, 143: 791
-
[6]
[6] Saha M, Pal A K. Tetrahedron Lett, 2011, 52: 4872
-
[7]
[7] Zarei A, Khazdooz L, Pirisedigh A, Hajipour A R, Seyedjamali H, Aghaei H. Tetrahedron Lett, 2011, 52: 4554
-
[8]
[8] Hajipour A R, Rafiee F. J Organomet Chem, 2011, 696: 2669
-
[9]
[9] Hajipour A R, Rafiee F. App Organomet Chem, 2011, 25: 542
-
[10]
[10] Karimi B, Enders D. Org Lett, 2006, 8: 1237
-
[11]
[11] Schönfelder D, Nuyken O, Weberskirch R. J Organomet Chem, 2005, 690: 4648
-
[12]
[12] Gruber-Woelfler H, Radaschitz P F, Feenstra P W, Haas W, Khinast J G. J Catal, 2012, 286: 30
-
[13]
[13] Polshettiwar V, Varma R S. Org Biomol Chem, 2009, 7: 37
-
[14]
[14] Polshettiwar V, Hesemann P, Moreau J J E. Tetrahedron, 2007, 63: 6784
-
[15]
[15] Uozumi Y, Kimura T. Synlett, 2002: 2045
-
[16]
[16] Bakherad M, Keivanloo A, Samangooei S. Chin. J. Catal (催化学报), 2014, 35: 324-328
-
[17]
[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]
[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]
[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]
[20] Yang X, Fei Z F, Zhao D, Ang W H, Li Y D, Dyson P J. Inorg Chem, 2008, 47: 3292
-
[21]
[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]
[22] Senapati K K, Roy S, Borgohain C, Phukan P. J Mol Catal A, 2012, 352: 128
-
[23]
[23] Proch S, Mei Y, Villanueva J M R, Lu Y, Karpov A, Ballauff M, Kempe R. Adv Synth Catal, 2008, 350: 493
-
[24]
[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]
[25] Ko S, Jang J. Angew Chem Int Ed, 2006, 45: 7564
-
[26]
[26] Costa N J S, Kiyohara P K, Monteiro A L, Coppel Y, Philippot K, Rossi L M. J Catal, 2010, 276: 382
-
[27]
[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]
[28] Cirtiu C M, Dunlop-Briere A F, Moores A. Green Chem, 2011, 13: 288
-
[29]
[29] Boudjahem A-G, Mokrane T, Redjel A, Bettahar M M. C R Chim, 2010, 13: 1433
-
[30]
[30] Yang H Q, Han X J, Li G, Wang Y W. Green Chem, 2009, 11: 1184
-
[31]
[31] Polshettiwar V, Molnár Á. Tetrahedron, 2007, 63: 6949
-
[32]
[32] Richardson J M, Jones C W. J Catal, 2007, 251: 80
-
[33]
[30] Zhao F Y, Shirai M, Ikushima Y, Arai M. J Mol Catal A, 2002, 180: 211
-
[1]
-
-
-
[1]
Jia-Cheng Hou , Hong-Tao Ji , Yu-Han Lu , Jia-Sheng Wang , Yao-Dan Xu , Yan-Yan Zeng , Wei-Min He . Sustainable and practical semi-heterogeneous photosynthesis of 5-amino-1,2,4-thiadiazoles over WS2/TEMPO. Chinese Chemical Letters, 2024, 35(8): 109514-. doi: 10.1016/j.cclet.2024.109514
-
[2]
Yiyue Ding , Qiuxiang Zhang , Lei Zhang , Qilu Yao , Gang Feng , Zhang-Hui Lu . Exceptional activity of amino-modified rGO-immobilized PdAu nanoclusters for visible light-promoted dehydrogenation of formic acid. Chinese Chemical Letters, 2024, 35(7): 109593-. doi: 10.1016/j.cclet.2024.109593
-
[3]
Peng Guo , Shicheng Dong , Xiang-Gui Zhang , Bing-Bin Yang , Jun Zhu , Ke-Yin Ye . Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates. Chinese Chemical Letters, 2025, 36(4): 110052-. doi: 10.1016/j.cclet.2024.110052
-
[4]
Heng Yang , Zhijie Zhou , Conghui Tang , Feng Chen . Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds. Chinese Chemical Letters, 2024, 35(6): 109257-. doi: 10.1016/j.cclet.2023.109257
-
[5]
Wen-Jing Li , Jun-Bo Wang , Yu-Heng Liu , Mo Zhang , Zhan-Hui Zhang . Molybdenum-doped carbon nitride as an efficient heterogeneous catalyst for direct amination of nitroarenes with arylboronic acids. Chinese Chemical Letters, 2025, 36(3): 110001-. doi: 10.1016/j.cclet.2024.110001
-
[6]
Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924
-
[7]
Mengli Xu , Zhenmin Xu , Zhenfeng Bian . Achieving Ullmann coupling reaction via photothermal synergy with ultrafine Pd nanoclusters supported on mesoporous TiO2. Chinese Journal of Structural Chemistry, 2024, 43(7): 100305-100305. doi: 10.1016/j.cjsc.2024.100305
-
[8]
Qijun Tang , Wenguang Tu , Yong Zhou , Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170
-
[9]
Xuhui Fan , Fan Wang , Mengjiao Li , Faiza Meharban , Yaying Li , Yuanyuan Cui , Xiaopeng Li , Jingsan Xu , Qi Xiao , Wei Luo . Visible light excitation on CuPd/TiN with enhanced chemisorption for catalyzing Heck reaction. Chinese Chemical Letters, 2025, 36(1): 110299-. doi: 10.1016/j.cclet.2024.110299
-
[10]
Peng Wang , Daijie Deng , Suqin Wu , Li Xu . Cobalt-based deep eutectic solvent modified nitrogen-doped carbon catalyst for boosting oxygen reduction reaction in zinc-air batteries. Chinese Journal of Structural Chemistry, 2024, 43(1): 100199-100199. doi: 10.1016/j.cjsc.2023.100199
-
[11]
Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
-
[12]
Xinlong Han , Huiying Zeng , Chao-Jun Li . Trifluoromethylative homo-coupling of carbonyl compounds. Chinese Chemical Letters, 2025, 36(1): 109817-. doi: 10.1016/j.cclet.2024.109817
-
[13]
Weichen Zhu , Wei Zuo , Pu Wang , Wei Zhan , Jun Zhang , Lipin Li , Yu Tian , Hong Qi , Rui Huang . Fe-N-C heterogeneous Fenton-like catalyst for the degradation of tetracycline: Fe-N coordination and mechanism studies. Chinese Chemical Letters, 2024, 35(9): 109341-. doi: 10.1016/j.cclet.2023.109341
-
[14]
Xueqi Zhang , Han Gao , Jianan Xu , Min Zhou . Polyelectrolyte-functionalized carbon nanocones enable rapid and accurate analysis of Ag nanoparticle colloids. Chinese Chemical Letters, 2025, 36(4): 110148-. doi: 10.1016/j.cclet.2024.110148
-
[15]
Kexin Yin , Jingren Yang , Yanwei Li , Qian Li , Xing Xu . Metal-free diatomaceous carbon-based catalyst for ultrafast and anti-interference Fenton-like oxidation. Chinese Chemical Letters, 2024, 35(12): 109847-. doi: 10.1016/j.cclet.2024.109847
-
[16]
Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
-
[17]
Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
-
[18]
Xin Huang , Yi Zhao , Wanzhen Liang . Vibronic coupling effect on intersystem crossing rates of TADF emitters. Chinese Journal of Structural Chemistry, 2024, 43(6): 100278-100278. doi: 10.1016/j.cjsc.2024.100278
-
[19]
Jian Ji , Jie Yan , Honggen Peng . Modulation of dinuclear site by orbital coupling to boost catalytic performance. Chinese Journal of Structural Chemistry, 2024, 43(8): 100360-100360. doi: 10.1016/j.cjsc.2024.100360
-
[20]
Yuehai Zhi , Chen Gu , Huachao Ji , Kang Chen , Wenqi Gao , Jianmei Chen , Dafeng Yan . The advanced development of innovative photocatalytic coupling strategies for hydrogen production. Chinese Chemical Letters, 2025, 36(1): 110234-. doi: 10.1016/j.cclet.2024.110234
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(334)
- HTML views(41)