Cellulose-supported N-heterocyclic carbene-palladium catalyst: Synthesis and its applications in the Suzuki cross-coupling reaction

Carbohydrate Polymers

Volumn 114, Issue , 2014, Pages 476-483

  Wang, Xiaoxia ^a   Hu, Peibo ^a   Xue, Fengjun ^a   Wei, Yuping ^a,b  

^a TIANJIN UNIVERSITY   (China)

^b Collaborative Innovation Center of Chemical Science and Engineering   (China)

Author keywords

Cellulose; N methylimidazole; Palladium; Suzuki cross coupling reaction

Indexed keywords

PALLADIUM;

ITS APPLICATIONS; N-HETEROCYCLIC; N-METHYLIMIDAZOLE; SUZUKI CROSS COUPLING REACTIONS;

CELLULOSE;

EID: 84906975368     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2014.08.030     Document Type: Article

References (55)

1. M.N.(née Gensow) Birkholz, Z. Freixa, and P.W.N.M. van Leeuwen Bite angle effects of diphosphines in CC and CX bond forming cross coupling reactions Chemical Society Reviews 38 2009 1099 1118
2. H.U. Blaser The chiral switch of (S)-metolachlor: A personal account of an industrial odyssey in asymmetric catalysis Advanced Synthesis and Catalysis 344 2002 17 31
3. C.M. Cirtiu, A.F. Dunlop-Brière, and A. Moores Cellulose nanocrystallites as an efficient support for nanoparticles of palladium: Application for catalytic hydrogenation and Heck coupling under mild conditions Green Chemistry 13 2011 288 291
4. D.J. Cole-Hamilton Homogeneous catalysis - New approaches to catalyst separation, recovery, and recycling Science 299 2003 1702 1706
5. J.P. Corbet, and G. Mignani Selected patented cross-coupling reaction technologies Chemical Reviews 106 2006 2651 2710
6. 4Journal of the American Chemical Society 127 2005 2485 2495
7. T. Drge, and F. Glorius The measure of all rings - N-Heterocyclic carbenes Angewandte Chemie International Edition 49 2010 6940 6952
8. Q. Du, and Y. Li Air-stable, recyclable, and time-efficient diphenylphosphinite cellulose-supported palladium nanoparticles as a catalyst for Suzuki-Miyaura reactions Beilstein Journal of Organic Chemistry 7 2011 378 385
9. Q. Du, and Y. Li Application of an air-and-moisture-stable diphenylphosphinite cellulose-supported nanopalladium catalyst for a Heck reaction Research on Chemical Intermediates 38 2012 1807 1817
10. C. Fleckenstein, S. Roy, S. Leuthäußer, and H. Plenio Sulfonated N-heterocyclic carbenes for Suzuki coupling in water Chemical Communications 2007 2870 2872
11. 3as ligands Accounts of Chemical Research 41 2008 1555 1564
12. W.J. Gammon, O. Kraft, A.C. Reilly, and B.C. Holloway Experimental comparison of N(1s) X-ray photoelectron spectroscopy binding energies of hard and elastic amorphous carbon nitride films with reference organic compounds Carbon 41 2003 1917 1923
13. T.T. Gao, A.P. Jin, and L.X. Shao N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed Mizoroki-Heck reaction of aryl chlorides with styrenes Beilstein Journal of Organic Chemistry 8 2012 1916 1919
14. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, and M. Lemaire Aryl-Aryl bond formation one century after the discovery of the Ullmann reaction Chemical Reviews 102 2002 1359 1469
15. W.A. Herrmann, M. Elison, J. Fischer, C. Köcher, and G.R.J. Artus Metal complexes of N-heterocyclic carbenes - A new structural principle for catalysts in homogeneous catalysis Angewandte Chemie International Edition in English 34 1995 2371 2374
16. W.A. Herrmann, C.P. Reisinger, and M. Spiegle Chelating N-heterocyclic carbene ligands in palladium-catalyzed heck-type reactions Journal of Organometallic Chemistry 557 1998 93 96
17. Y. He, and C. Cai A simple procedure for the polymer-supported N-heterocyclic carbene-rhodium complex via click chemistry: A recyclable catalyst for the addition of arylboronic acids to aldehydes Chemical Communications 47 2011 12319 12321
18. J. Hu, and Y. Liu Pd nanoparticle aging and its implications in the Suzuki cross-coupling reaction Langmuir 21 2005 2121 2123
19. N. Jamwal, R.K. Sodhi, P. Gupta, and S. Paul Nano Pd(0) supported on cellulose: A highly efficient and recyclable heterogeneous catalyst for the Suzuki coupling and aerobic oxidation of benzyl alcohols under liquid phase catalysis International Journal of Biological Macromolecules 49 2011 930 935
20. T. Kang, Q. Feng, and M. Luo An active and recyclable polystyrene-supported N-heterocyclic carbene-palladium catalyst for the Suzuki reaction of arylbromides with arylboronic acids under mild conditions Synlett 2005 2305 2308
21. S. Keshipour, S. Shojaei, and A. Shaabani Palladium nano-particles supported on ethylenediamine functionalized cellulose as a novel and efficient catalyst for the Heck and Sonogashira couplings in water Cellulose 20 2013 973 980
22. V.N. Khabashesku, J.L. Zimmerman, and J.L. Margrave Powder synthesis and characterization of amorphous carbon nitride Chemistry of Materials 12 2000 3264 3270
23. J.H. Kim, J.W. Kim, M. Shokouhimehr, and Y.S. Lee Polymer-supported N-heterocyclic carbene-palladium complex for heterogeneous Suzuki cross-coupling reaction Journal of Organic Chemistry 70 2005 6714 6720
24. J.W. Kim, J.H. Kim, D.H. Lee, and Y.S. Lee Amphiphilic polymer supported N-heterocyclic carbene palladium complex for Suzuki cross-coupling reaction in water Tetrahedron Letters 47 2006 4745 4748
25. D. Klemm, B. Heublein, H.-P. Fink, and A. Bohn Cellulose: Fascinating biopolymer and sustainable raw material Angewandte Chemie International Edition 44 2005 3358 3393
26. R. Kurt, R. Sanjines, A. Karimi, and F. Lévy Structural and mechanical properties of CNx thin films prepared by magnetron sputtering Diamond and Related Materials 9 2000 566 572
27. G. Lázaro, F.J. Fernández-Alvarez, M. Iglesias, C. Horna, E. Vispe, and R. Sancho Heterogeneous catalysts based on supported Rh-NHC complexes: Synthesis of high molecular weight poly(silyl ether)s by catalytic hydrosilylation Catalysis Science & Technology 4 2014 62 70
28. J. Lemo, K. Heuze, and D. Astruc Efficient dendritic diphosphino Pd(II) catalysts for the suzuki reaction of chloroarenes Organic Letters 7 2005 2253 2256
29. A.F. Littke, and G.C. Fu Palladium-catalyzed coupling reactions of aryl chlorides Angewandte Chemie International Edition 41 2002 4176 4211
30. X. Li, H. Wang, J.T. Robinson, H. Sanchez, G. Diankov, and H. Dai Simultaneous nitrogen doping and reduction of graphene oxide Journal of the American Chemical Society 131 2009 15939 15944
31. Y. Li, X.M. Hong, D.M. Collard, and M.A. El-Sayed Suzuki cross-coupling reactions catalyzed by palladium nanoparticles in aqueous solution Organic Letters 2 2000 2385 2388
32. H.K. Lo, and F.T. Luo Synthesis of PS-supported NHC-Pd catalyst derived from theobromine and its applications in Suzuki-Miyaura reaction Journal of the Chinese Chemical Society 59 2012
33. 2-supported chiral imidazole thioether ligand palladium catalyst Chinese Journal of Chemistry 31 2011 1828 1834
34. N. Marion, and S.P. Nolan N-Heterocyclic carbenes in gold catalysis Chemical Society Reviews 37 2008 1776 1782
35. R. Martin, and S.L. Buchwald Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands Accounts of Chemical Research 41 2008 1461 1473
36. A.de Meijere, and F. Diederich Metal-catalyzed cross-coupling reactions 2004 Wiley-VCH Weinheim, Germany
37. N. Miyaura, and A. Suzuki Palladium-catalyzed cross-coupling reactions of organoboron compounds Chemical Reviews 95 1995 2457 2483
38. Á. Molnár, and A. Papp The use of polysaccharides and derivatives in palladium-catalyzed coupling reactions Catalysis Science & Technology 4 2014 295
39. R. Narayanan, and M.A. El-Sayed Effect of catalysis on the stability of metallic nanoparticles: Suzuki reaction catalyzed by PVP-palladium nanoparticles Journal of the American Chemical Society 125 2003 8340 8347
40. D.W. Old, J.P. Wolfe, and S.L. Buchwald A highly active catalyst for palladium-catalyzed cross-coupling reactions: Room-temperature Suzuki couplings and amination of unactivated aryl chlorides Journal of the American Chemical Society 120 1998 9722 9723
41. C.D. Pozo, A. Corma, M. Iglesias, and F. Sánchez Recyclable mesoporous silica-supported chiral ruthenium-(NHC)NN-pincer catalysts for asymmetric reactions Green Chemistry 13 2011 2471 2481
42. K. Rahn, M. Diamantoglou, D. Klemm, H. Berghmans, and T. Heinze Homogeneous synthesis of cellulose p-toluenesulfonates in N,N-dimethylacetamidel LiCl solvent system Angewandte Makromolekulare Chemie 238 1996 143 163
43. K.R. Reddy, N.S. Kumar, P.S. Reddy, B. Sreedhar, and M.L. Kantam Cellulose supported palladium(0) catalyst for Heck and Sonogashira coupling reactions Journal of Molecular Catalysis A: Chemical 252 2006 12 16
44. S. Rodil, N.A. Morrison, W.I. Milne, J. Robertson, V. Stolojan, and D.N. Jayawardane Deposition of carbon nitride films using an electron cyclotron wave resonance plasma source Diamond and Related Materials 9 2000 524 529
45. E. Sin, S. Yi, and Y. Lee Chitosan-g-mPEG-supported palladium (0) catalyst for Suzuki cross-coupling reaction in water Journal of Molecular Catalysis A: Chemical 315 2010 99 104
46. A. Suzuki Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995-1998 Journal of Organometallic Chemistry 576 1999 147 168
47. Z.Y. Wang, G.Q. Chen, and L.X. Shao N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed Suzuki-Miyaura coupling of aryl sulfonates with arylboronic acids Journal of Organic Chemistry 77 2012 6608 6614
48. X. Wu, C. Lu, W. Zhang, G. Yuan, R. Xiong, and X. Zhang A novel reagentless approach for synthesizing cellulose nanocrystal-supported palladium nanoparticles with enhanced catalytic performance Journal of Materials Chemistry A 1 2013 8645 8652
49. 4/Ag nanocomposites with catalytic and antibacterial activity Journal of Materials Chemistry A 1 2013 14910 14918
50. Y. Xu, X. Wang, and Y. Wei Heck coupling reactions of aryl halides with acrylates catalyzed by cellulose-supported triphenylphosphine palladium nanoparticles Chemistry & Bioengineering 1 2014 43 47
51. Y. Xu, L. Zhang, and Y. Cui Catalytic performance of cellulose supported palladium complex for heck reaction in water Journal of Applied Polymer Science 110 2008 2996 3000
52. L. Yin, and J. Liebscher Carbon-carbon coupling reactions catalyzed by heterogeneous palladium catalysts Chemical Reviews 107 2007 133 173
53. C. Zhang, J. Huang, M.L. Trudell, and S.P. Nolan Palladium-imidazol-2-ylidene complexes as catalysts for facile and efficient Suzuki cross-coupling reactions of aryl chlorides with arylboronic acids Journal of Organic Chemistry 64 1999 3804 3805
54. X.A. Zhao, C.W. Ong, Y.C. Tsang, Y.W. Wong, P.W. Chan, and C.L. Choy Reactive pulsed laser deposition of CNx films Applied Physics Letters 66 1995 2652 2654
55. C. Zheng, Y. Li, and W. Zheng Ethylenediamine-functionalized cellulose supported nano-palladium for suzuki reaction Chinese Journal of Chemistry 29 2009 1983 1987