A nanoparticulate polyacetylene-supported Pd(Ⅱ) catalyst combining the advantages of homogeneous and heterogeneous catalysts

doi:10.1016/S1872-2067(15)60930-5

Abstract

Abstract:

A novel nanoparticulate polyacetylene-supported Pd(Ⅱ) catalyst (NP-Pd(Ⅱ)) for use in the aqueous Suzuki-Miyaura cross coupling reaction was successfully synthesized by simply treating an aqueous solution of PdCl₄^2- with acetylene under ambient conditions. Electron microscopy, Fourier transform infrared spectroscopy, Raman spectroscopy, X-ray diffraction, X-ray photoelectron spectroscopy and X-ray absorption spectroscopy were employed to characterize the NP-Pd(Ⅱ) structure in detail. These analyses demonstrated that the Pd atoms in the NP-Pd(Ⅱ) were present as Pd(Ⅱ) and were coordinated with both the Cl atoms and the C=C bonds of the polyacetylene. Both the homogeneous distribution of the Pd(Ⅱ) along the polyacetylene backbone and the aggregation of the NP-Pd(Ⅱ) in solution work in conjunction to make this material an ideal catalyst, combining the advantages of both homogeneous and heterogeneous catalysts.

Key words: Suzuki coupling, Acetylene, Palladium complex, Aqueous reaction

Huan Li, Guangxu Chen, Paul N. Duchesne, Peng Zhang, Yan Dai, Huayan Yang, Binghui Wu, Shengjie Liu, Chaofa Xu, Nanfeng Zheng. A nanoparticulate polyacetylene-supported Pd(Ⅱ) catalyst combining the advantages of homogeneous and heterogeneous catalysts[J]. Chinese Journal of Catalysis, 2015, 36(9): 1560-1572.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(15)60930-5

https://www.cjcatal.com/EN/Y2015/V36/I9/1560

References

[1] Wijngaarden R I, Westerterp K R, Kronberg A, Bos A. Industrial catalysis: Optimizing Catalysts and Processes. Weiheim: Wiley, 2008
[2] Bhaduri S, Mukesh D. Homogeneous Catalysis: Mechanism and Industrial Applications. Weiheim: Wiley, 2000
[3] Van Leeuwen P W N M, Leeuwen P W. Homogeneous Catalysis: Understanding the Art. New York: Springer, 2005
[4] Trost B M. Angew Chem Int Ed, 1995, 34: 259
[5] Behr A, Neubert P. Applied Homogeneous Catalysis. Weiheim: Wiley, 2012
[6] Cole-Hamilton D J. Science, 2003, 299: 1702
[7] Ertl G, Knozinger H, Schuth F, Weitkamp J. Handbook of Heterogeneous Catalysis. Weiheim: Wiley, 2008
[8] Molnar A. Chem Rev, 2011, 111: 2251
[9] Polshettiwar V, Len C, Fihri A. Coord Chem Rev, 2009, 253: 2599
[10] Lu J, Toy P H. Chem Rev, 2009, 109: 815
[11] McMorn P, Hutchings G J. Chem Soc Rev, 2004, 33: 108
[12] Collis A E, Horvath I T. Catal Sci Technol, 2011, 1: 912
[13] Phan N T S, Van Der Sluys M, Jones C W. Adv Synth Catal, 2006, 348: 609
[14] Pagliaro M, Pandarus V, Ciriminna R, Beland F, Demma Carà P. ChemCatChem, 2012, 4: 432
[15] Johansson Seechurn C C, Kitching M O, Colacot T J, Snieckus V. Angew Chem Int Ed, 2012, 51: 5062
[16] Miyaura N. Top Curr Chem, 2002, 219: 11
[17] Suzuki A. J Organomet Chem, 1999, 576: 147
[18] Nicolaou K C, Bulger P G, Sarlah D. Angew Chem Int Ed, 2005, 44: 4442
[19] Miyaura N, Suzuki A. Chem Rev, 1995, 95: 2457
[20] Magano J, Dunetz J R. Chem Rev, 2011, 111: 2177
[21] Kambe N, Iwasaki T, Terao J. Chem Soc Rev, 2011, 40: 4937
[22] Littke A F, Fu G C. Angew Chem Int Ed, 1998, 37: 3387
[23] Surry D S, Buchwald S L. Chem Sci, 2011, 2: 27
[24] Wu X F, Neumann H, Beller M. ChemSusChem, 2013, 6: 229
[25] Böhm V P W, Gstöttmayr C W K, Weskamp T, Herrmann W A. J Organomet Chem, 2000, 595: 186
[26] Marion N, Nolan S P. Acc Chem Res, 2008, 41: 1440
[27] Valente C, Calimsiz S, Hoi K H, Mallik D, Sayah M, Organ M G. Angew Chem Int Ed, 2012, 51: 3314
[28] Nájera C, Gil-Moltó J, Karlström S, Falvello L R. Org Lett, 2003, 5: 1451
[29] Buchmeiser M R, Wurst K. J Am Chem Soc, 1999, 121: 11101
[30] Beletskaya I P, Cheprakov A V. J Organomet Chem, 2004, 689: 4055
[31] Kim K S, Gossmann A F, Winograd N. Anal Chem, 1974, 46: 197
[32] Kumar G, Blackburn J R, Albridge R G, Moddeman W E, Jones M M. Inorg Chem, 1972, 11: 296
[33] Wang X F, Andrews L. J Phys Chem A, 2003, 107: 337
[34] Maitlis P M. Acc Chem Res, 1976, 9: 93
[35] Abraham R, Mobli M. Modelling ¹H NMR Spectra of Organic Compounds. Weinheim: Wiley, 2008
[36] Elding L. Inorg Chim Acta, 1972, 6: 647
[37] Lichtmann L S, Imhoff E A, Sarhangi A, Fitchen D B. J Chem Phys, 1984, 81: 168
[38] McIntire M, Zhao L, Kobryanskii V, Chronister E. J Raman Spectrosc, 2011, 42: 1435
[39] Grogan M J, Nakamoto K. J Am Chem Soc, 1968, 90: 918
[40] Cooper D G, Powell J. Inorg Chem, 1976, 15: 1959
[41] Bernard G M, Wasylishen R E, Phillips A D. J Phys Chem A, 2000, 104: 8131
[42] Bennett M A. Chem Rev, 1962, 62: 611
[43] Jain V K, Jain L. Coord Chem Rev, 2005, 249: 3075
[44] Hartley F R. Chem Rev, 1969, 69: 799
[45] Sobczak J W, Sobczak E, Lesiak B, Palczewska W, Kosinski A. J Alloy Compd, 1999, 286: 98
[46] Negishi E I, De Meijene A. Handbook of Organopalladium Chemistry for Organic Synthesis. Weinheim: Wiley, 2002
[47] Fairlamb I J S. Org Biomol Chem, 2008, 6: 3645
[48] Scheuermann G M, Rumi L, Steurer P, Bannwarth W, Mülhaupt R. J Am Chem Soc, 2009, 131: 8262
[49] Lamblin M, Nassar-Hardy L, Hierso J C, Fouquet E, Felpin F X. Adv Synth Catal, 2010, 352: 33
[50] Polshettiwar V, Decottignies A, Len C, Fihri A. ChemSusChem, 2010, 3: 502
[51] Badone D, Baroni M, Cardamone R, Ielmini A, Guzzi U. J Org Chem, 1997, 62: 7170
[52] Uozumi Y, Nakai Y. Org Lett, 2002, 4: 2997
[53] Ganesamoorthy S, Shanmugasundaram K, Karvembu R. J Mol Catal A, 2013, 371: 118
[54] Liu C, Zhang Y X, Liu N, Qiu J S. Green Chem, 2012, 14: 2999
[55] Leadbeater N E. Chem Commun, 2005: 2881