Suzuki Reaction of Aryl Bromides Using a Phosphine-Free Magnetic Nanoparticle-Supported Palladium Catalyst

doi:10.1016/S1872-2067(10)60270-7

摘要/Abstract

摘要： A palladium catalyst immobilized on superparaganetic nanoparticles was prepared with a palladium loading of 0.30 mmol/g. The catalyst was characterized using X-ray diffraction, scanning electron microscopy, transmission electron microscopy, vibrating sample magnetometry, thermogravimetric analysis, Fourier transform infrared, atomic absorption spectrophotometry, and nitrogen adsorption. The immobilized palladium catalyst was an efficient catalyst without added phosphine ligands for the Suzuki cross-coupling reaction of several aryl bromides with phenylboronic acid. The recovery of catalyst was simply by magnetic decantation in the presence of a magnet. The immobilized palladium catalyst can be reused many times without significant degradation in catalytic activity. No leaching of active palladium species into the reaction solution was detected.

关键词: superparamagnetic nanoparticle, Suzuki reaction, palladium, aryl bromide

Abstract: A palladium catalyst immobilized on superparaganetic nanoparticles was prepared with a palladium loading of 0.30 mmol/g. The catalyst was characterized using X-ray diffraction, scanning electron microscopy, transmission electron microscopy, vibrating sample magnetometry, thermogravimetric analysis, Fourier transform infrared, atomic absorption spectrophotometry, and nitrogen adsorption. The immobilized palladium catalyst was an efficient catalyst without added phosphine ligands for the Suzuki cross-coupling reaction of several aryl bromides with phenylboronic acid. The recovery of catalyst was simply by magnetic decantation in the presence of a magnet. The immobilized palladium catalyst can be reused many times without significant degradation in catalytic activity. No leaching of active palladium species into the reaction solution was detected.

Key words: superparamagnetic nanoparticle, Suzuki reaction, palladium, aryl bromide

Nghia T. BUI, Trung B. DANG, Ha V. LE, Nam T. S. PHAN. Suzuki Reaction of Aryl Bromides Using a Phosphine-Free Magnetic Nanoparticle-Supported Palladium Catalyst[J]. 催化学报, 2011, 32(11): 1667-1676.

Nghia T. BUI, Trung B. DANG, Ha V. LE, Nam T. S. PHAN. Suzuki Reaction of Aryl Bromides Using a Phosphine-Free Magnetic Nanoparticle-Supported Palladium Catalyst[J]. Chinese Journal of Catalysis, 2011, 32(11): 1667-1676.

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参考文献

1Paul S, Clark J H. Green Chem, 2003, 5: 635
2Nicolaou K C, Bulger P G, Sarlah D. Angew Chem, Int Ed, 2005, 44: 4442
3Miyaura N, Suzuki A. Chem Rev, 1995, 95: 2457
4Cai M, Sha J, Xu Q. J Mol Catal A, 2007, 268: 82
5Bellina F, Carpita A, Rossi R. Synthesis, 2004: 2419
6Phan N T S, van der Sluys M, Jones C W. Adv Synth Catal, 2006, 348: 609
7Corbet J-P, Mignani G. Chem Rev, 2006, 106: 2651
8Beletskaya I P, Cheprakov A V. Chem Rev, 2000, 100: 3009
9Leadbeater N E, Marco M. Chem Rev, 2002, 102: 3217
10Kim J-W, Kim J-H, Lee D-H, Lee Y-S. Tetrahedron Lett, 2006, 47: 4745
11Islam S M, Mondal P, Roy A S, Mondal S, Hossain D. Tetra-hedron Lett, 2010, 51: 2067
12Phan N T S, Styring P. Green Chem, 2008, 10: 1055
13Karimi B, Akhavan P F. Chem Commun, 2009: 3750
14Yang H, Han X, Li G, Ma Z, Hao Y. J Phys Chem C, 2010, 114: 22221
15Al-Hashimi M, Qazi A, Sullivan A C, Wilson J R H. J Mol Catal A, 2007, 278: 160
16Glasspoole B W, Webb J D, Crudden C M. J Catal, 2009, 265: 148
17Jana S, Haldar S, Koner S. Tetrahedron Lett, 2009, 50: 4820
18Qiu H, Sarkar S M, Lee D-H, Jin M-J. Green Chem, 2008, 10: 37
19Shi S, Zhang Y. Green Chem, 2008, 10: 868
20Yang H, Han X, Ma Z, Wang R, Liu J, Ji X. Green Chem, 2010, 12: 441
21Dhara K, Sarkar K, Srimani D, Saha S K, Chattopadhyay P, Bhaumik A. Dalton Trans, 2010, 39: 6395
22Okumura K, Tomiyama T, Okuda S, Yoshida H, Niwa M. J Catal, 2010, 273: 156
23Durap F, Rakap M, Aydemir M, Özkar S, Appl Catal A, 2010, 382: 339
24Jin M-J, Taher A, Kang H-J, Choi M, Ryoo R. Green Chem, 2009, 11: 309
25Trilla M, Pleixats R, Man M W C, Bied C, Moreau J J E. Tet-rahedron Lett, 2006, 47: 2399
26Blanco B, Brissart M, Moreno-Mañas M, Pleixats R, Mehdi A, Reyé C, Bouquillon S, Hénin F, Muzart J. Appl Catal A, 2006, 297: 117
27Scheuermann G M, Rumi L, Steurer P, Bannwarth W, Mül-haupt R. J Am Chem Soc, 2009, 131: 8262
28Søbjerg L S, Gauthier D, Lindhardt A T, Bunge M, Finster K, Meyer R L, Skrydstrup T. Green Chem, 2009, 12: 2041
29Prastaro A, Ceci P, Chiancone E, Boffi A, Cirilli R, Colone M, Fabrizi G, Stringaro A, Cacchi S. Green Chem, 2009, 11: 1929
30Chattopadhyay K, Dey R, Ranu B C. Tetrahedron Lett, 2009, 50: 3164
31Das D D, Sayari A. J Catal, 2007, 246: 60
32Yan W, Mahurin S M, Pan Z, Overbury S H, Dai S. J Am Chem Soc, 2005, 127: 10480
33Astruc D, Lu F, Aranzaes J R. Angew Chem, Int Ed, 2005, 44: 7852
34Phan N T S, Jones C W. J Mol Catal A, 2006, 253: 123
35Phan N T S, Gill C S, Nguyen J V, Zhang Z J, Jones C W. Angew Chem, Int Ed, 2006, 45: 2209
36Lim C W, Lee I S. Nano Today, 2010, 5: 412
37Shylesh S, Schunemann V, Thiel W R. Angew Chem, Int Ed, 2010, 49: 3428
38Yoon T-J, Lee W, Oh Y-S, Lee J-K. New J Chem, 2003, 27: 227
39Polshettiwar V, Baruwati B, Varma R S. Green Chem, 2009, 11: 127
40Lu A H, Schmidt W, Matoussevitch N, Bonnemann H, Spli-ethoff B, Tesche B, Bill E, Kiefer W, Schuth F. Angew Chem, Int Ed, 2004, 43: 4303
41Hu A, Yee G T, Lin W. J Am Chem Soc, 2005, 127: 12486
42Panella B, Vargas A, Baiker A. J Catal, 2009, 261: 88.
43Niu F, Zhang L, Luo S-Z, Song W-G. Chem Commun, 2010, 46: 1109
44Stevens P D, Fan J, Gardimalla H M R, Yen M, Gao Y. Org Lett, 2005, 7: 2085
45Laska U, Frost C G, Price G J, Plucinski P K. J Catal, 2009, 268: 318
46Zhang Y-Q, Wei X-W, Yu R. Catal Lett, 2010, 135: 256
47Baruwati B, Guin D, Manorama S V. Org Lett, 2007, 9: 5377
48Yuan D, Zhang Q, Dou J. Catal Commun, 2010, 11: 606
49Liu J, Peng X, Sun W, Zhao Y, Xia C. Org Lett, 2008, 10: 3933
50Phan N T S, Le H V. J Mol Catal A, 2011, 334: 130
51Hara T, Kaneta T, Mori K, Mitsudome T, Mizugaki T, Ebitani K, Kaneda K. Green Chem, 2007, 9: 1246
52Zhang S, Zhao X, Niu H, Shi Y, Cai Y, Jiang G. J Hazard Mater, 2009, 167: 560
53Dutta B, Jana S, Bhattacharjee A, Gütlich P, Iijima S-I, Koner S. Inorg Chim Acta, 2010, 363: 696
54Oliveira R L, Kiyohara P K, Rossi L M. Green Chem, 2010, 12: 144
55Long W, Gill C S, Choi S, Jones C W. Dalton Trans, 2010, 39: 1470
56Che C, Li W, Lin S, Chen J, Zheng J, Wu J-C, Zheng Q, Zhang G, Yang Z, Jiang B. Chem Commun, 2009: 5990
57Zheng X, Luo S, Zhang L, Cheng J-P. Green Chem, 2009, 11: 455
58Gao X, Yu K M K, Tam K Y, Tsang S K. Chem Commun, 2003: 2998
59Netto C G C M, Andrade L H, Toma H E. Tetrahedron: Asymmetry, 2009, 20: 2299
60Jiang Y, Guo C, Xia H, Mahmood I, Liu C, Liu H. J Mol Catal B, 2009, 58: 103
61Lee K S, Woo M H, Kim H S, Lee E Y, Lee I S. Chem Com-mun, 2009: 3780
62Shen X C, Fang X Z, Zhou Y H, Liang H. Chem Lett, 2004, 33: 1468
63Gronnow M J, Luque R, Macquarrie D J, Clark J H. Green Chem, 2005, 7: 552
64Choudhary D, Paul S, Guptaa R, Clark J H. Green Chem, 2006, 8: 479
65Rondinone A J, Samia A C S, Zhang Z J. J Phys Chem B, 1999, 103: 6876
66Lia X, Kutal C. J Alloy Compd, 2003, 349: 264
67Gill C S, Price B A, Jones C W. J Catal, 2007, 251: 145
68Ma M, Zhang Y, Yu W, Shen H Y, Zhang H Q, Gu N. Colloids Surf A, 2003, 212: 219
69Shen X C, Fang X Z, Zhou Y H, Liang H. Chem Lett, 2004, 33: 1468
70Watanabe T, Miyaura N, Suzuki A. Synlett, 1992: 207
71Zhong C, Sasaki T, Tada M, Iwasawa Y. J Catal, 2006, 242: 357
72Sicre C, Alonso-Gómez J-L, Cid M M. Tetrahedron, 2006, 62: 11063
73Schröter S, Stock C, Bach T. Tetrahedron, 2005, 61: 2245
74Fairlamb I J S. Annu Rep Prog Chem, Sect B, 2005, 101: 69
75Das P, Bora U, Tairai A, Sharma C. Tetrahedron Lett, 2010, 51: 1479
76Guo M, Zhang Q. Tetrahedron Lett, 2009, 50: 1965
77Bedford R B, Hazelwood S L, Fimmert M E, Albisson D A, Draper S M, Scully P N, Coles S J, Hursthouse M B. Chem-Eur J, 2003, 9: 3216
78Phan N T S, Brown D H, Adams H, Sharon E S, Styring P. Dalton Trans, 2004: 1348
79Phan N T S, Brown D H, Styring P. Green Chem, 2004, 6: 526

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