New zirconium hydrogen phosphate alkyl and/or aryl phosphonates with high surface area as heterogeneous Brønsted acid catalysts for aza-Diels-Alder reaction in aqueous medium

Journal of Catalysis

Volumn 277, Issue 1, 2011, Pages 80-87

  Lanari, Daniela ^a   Montanari, Francesca ^a   Marmottini, Fabio ^a   Piermatti, Oriana ^a   Orr, Mara ^a   Vaccaro, Luigi ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

Aqueous medium; Aza Diels Alder reaction; Br nsted acid catalysis; Heterogeneous catalysis; Zirconium phosphate

Indexed keywords

ACID CATALYST; ACIDIC SITES; AMORPHOUS SOLIDS; AQUEOUS MEDIUM; CATALYTIC ACTIVITY; DIELS-ALDER REACTION; HETEROGENEOUS CATALYSIS; HIGH SURFACE AREA; HYDROPHOBIC GROUPS; MESOPOROUS; PHOSPHONATES; SOLID CATALYSTS; SOLID STRUCTURES; SURFACE AREA; ZIRCONIUM HYDROGEN PHOSPHATE; ZIRCONIUM PHOSPHATE;

ALKYLATION; CATALYSIS; ELECTROCHEMICAL SENSORS; HYDROGEN; HYDROPHOBICITY; PHOSPHATES; PHOTOCHEMICAL REACTIONS; ZIRCONIUM; ZIRCONIUM COMPOUNDS;

CATALYST ACTIVITY;

EID: 78650179763     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2010.10.012     Document Type: Article

References (78)

1. K. Zhu, D. Wang, and J. Liu Nano Res. 2 2009 1
2. J.L. White, and M.J. Truitt Progr. Nucl. Magn. Res. Spett. 51 2007 139
3. R.A. Sheldon, and R.S. Dowing Appl. Catal. A: Gen. 189 1999 163
4. A. Finiels, P. Geneste, J. Lecomte, F. Marichez, C. Moreau, and P. Moreau J. Mol. Catal. A: Chem. 148 1999 165
5. P.S. Sreeprasanth, R. Srivastara, D. Srinivas, and P. Ratnasamy Appl. Catal. A: Gen. 314 2006 148
6. S. Namba, Y. Wakushima, T. Shimizu, H. Masumoto, and T. Yashima Stud. Surf. Sci. Catal. 20 1985 205
7. J. Lecomte, A. Finiels, P. Geneste, and C. Moreau J. Mol. Catal. A: Chem. 140 1999 157
8. J.M. Thomas, and R. Raja Annu. Rev. Mater. Res. 35 2005 315
9. T. Okuhara Chem. Rev. 102 2002 3641
10. A. Clearfielf, and U. Costantino G. Alberti, T. Bein, Comprehensive Supramolecular Chemistry vol. 7 1996 Pergamon Press Oxford 107
11. G. Alberti, M. Casciola, U. Costantino, and R. Vivani Adv. Mater. 8 1996 291
12. R. Vivani, F. Costantino, G. Alberti, and M. Nocchetti Micropor. Mesopor. Mater. 107 2008 58
13. M. Curini, O. Rosati, and U. Costantino Curr. Org. Chem. 2004 591
14. A. Clearfield, and Z. Wang J. Chem. Soc. Dalton Trans. 2002 2937
15. A. Clearfield Dalton Trans. 2008 6089
16. F. Benvenuti, C. Carlini, P. Patrono, A.M. Raspolli Galletti, G. Sbrana, M.A. Massucci, and P. Galli Appl. Catal. A: Gen. 193 2000 147
17. Z. Wang, J.M. Heising, and A. Clearfield J. Am. Chem. Soc. 125 2003 10375
18. U. Costantino, F. Fringuelli, M. Nocchetti, and O. Piermatti App. Catal. A: Gen. 326 2007
19. U. Costantino, F. Fringuelli, M. Orr, M. Nocchetti, O. Piermatti, and F. Pizzo Eur. J. Org. Chem. 2009 1214
20. Cipiciani, U. Costantino, F. Bellezza, F. Fringuelli, M. Orr, O. Piermatti, and F. Pizzo Catal. Today 152 2010 61
21. N. Kumada, T. Nakatani, Y. Yonesaki, T. Takei, and N. Kinomura J. Mater. Sci. 43 2008 2206
22. J.-H. Jung, and H.-J. Sohn Micropor. Mesopor. Mater. 106 2007 49
23. Y. Feng, W. He, X. Zhang, X. Jia, and H. Zhao Mater. Lett. 61 2007 3258
24. X. Shi, J. Liu, C. Li, and Q. Yang Inorg. Chem. 46 2007 7944
25. S. Bonollo, F. Fringuelli, F. Pizzo, and L. Vaccaro Synlett 2008 1574 For some examples of processes in water see
26. S. Bonollo, F. Fringuelli, F. Pizzo, and L. Vaccaro Synlett 2007 2683
27. S. Bonollo, F. Fringuelli, F. Pizzo, and L. Vaccaro Green Chem. 8 2006 960
28. F. Fringuelli, F. Pizzo, S. Tortoioli, and L. Vaccaro Org. Lett. 7 2005 4411
29. F. Fringuelli, F. Pizzo, and L. Vaccaro J. Org. Chem. 69 2004 2315
30. G. Fioroni, F. Fringuelli, F. Pizzo, and L. Vaccaro Green Chem. 5 2003 425
31. T. Angelini, F. Fringuelli, D. Lanari, and L. Vaccaro Tetrahedron Lett. 51 2010 1566 For some examples of processes under solvent-free conditions see
32. F. Fringuelli, D. Lanari, F. Pizzo, and L. Vaccaro Green Chem. 12 2010 203
33. F. Fringuelli, D. Lanari, F. Pizzo, and L. Vaccaro Curr. Org. Synth. 6 2009 203
34. R. Ballini, L. Barboni, L. Castrica, F. Fringuelli, D. Lanari, F. Pizzo, and L. Vaccaro Adv. Synth. Cat. 350 2008 1218
35. F. Fringuelli, D. Lanari, F. Pizzo, and L. Vaccaro Eur. J. Org. Chem. 2008 3928
36. R. Ballini, G. Bosica, A. Palmieri, F. Pizzo, and L. Vaccaro Green Chem. 10 2008 541
37. F. Fringuelli, R. Girotti, O. Piermatti, F. Pizzo, and L. Vaccaro Org. Lett. 8 2006 5741
38. G. Alberti, M.G. Bernasconi, M. Casciola, and U. Costantino J. Inorg. Nucl. Chem. 42 1980 1631
39. F. Bellezza, A. Cipiciani, U. Costantino, and F. Marmottini Langmuir 22 2006 5064
40. R.J. Sundberg, and S.Q. Smith G.A. Cordell, The Alkaloids vol. 59 2002 Academic Press 261
41. D. O'Hagan Nat. Prod. Rep. 17 2000 435
42. D.L. Boger, and S.M. Weinreb Hetero Diels-Alder Methodology in Organic Synthesis 1987 Academic Press San Diego, CA
43. C.J. Li, and T.H. Chan Organic Reaction in Aqueous Media 1997 Whiley NY
44. P.T. Anastas Green Chemistry: Theory and Practice 1998 Oxford University Press Oxford
45. P.A. Grieco, Organic Synthesis in Water 1998 Blackie Academic and Professional London
46. F. Fringuelli, O. Piermatti, F. Pizzo, and L. Vaccaro Eur. J. Org. Chem. 2001 439
47. S. Kobayashhi, and K. Manabe Chem. Eur. J. 8 2002 4095
48. F. Fringuelli, O. Piermatti, F. Pizzo, and L. Vaccaro Current Org. Chem. 7 2003 1661
49. C.J. Li Chem. Rev. 105 2005 3095
50. U.M. Lindstrom, Organic Reaction in Water 2007 Blackwell Publishing
51. R. Ballini, L. Barboni, F. Fringuelli, A. Palmieri, F. Pizzo, and L. Vaccaro Green Chem. 9 2007 823
52. M. Gruttadauria, F. Giacalone, and R. Noto Adv. Synth. Catal. 351 2009 33
53. G. Babu, and P.T. Perumal Tetrahedron 54 1998 1627
54. G. Shanthi, and P.T. Perumal Synth. Commun. 2005 1319
55. H. Sundén, I. Ibrahem, L. Eriksson, and A. Cordova Angew. Chem. Int. Ed. 44 2005 4877
56. H. Liu, L.F. Cun, A.Q. Mi, Y.Z. Jiang, and L.Z. Gong Org. Lett. 8 2006 6023
57. M. Rueping, and C. Azap Angew. Chem. Int. Ed. 45 2006 7832
58. A.S. Luis, G.A. Vallejos, N. Correa, G.C. Margarita, W. de la Guarda, and V.V. Kouznetsov Lett. Org. Chem. 5 2008 559
59. H. Yang, and R.G. Carter J. Org. Chem. 74 2009 5151
60. N. Takenaka, Y. Huang, and V. Rawal Tetrahedron 58 2002 8299
61. D.M. Hodgson, and J.-M. Galano Org. Lett. 7 2005 2221
62. M.O.F. Khan, M.S. Levi, B.L. Tekwani, N.H. Wilson, and R.F. Borne Bioorg. Med. Chem. 15 2007 3919
63. M.O.F. Khan, M.S. Levi, C.R. Clark, S.Y. Ablordeppey, S.J. Law, N.H. Wilson, and R.F. Borne Stud. Nat. Prod. Chem. 34 2008 753
64. S.G. Gregg, and K.S. Sing Adsorption Surface Area and Porosity 2nd ed. 1982 Academic Press
65. S. Lowell, and J.E. Shields Powder Surface Area and Porosity third ed. 1991 Chapman and Hall
66. S. Brunauer, P.H. Emmett, and E. Teller J. Am. Chem. Soc. 60 1938 309
67. B.C. Lippens, and J.H.J. de Boer Catalysis 4 1965 319
68. F. Marmottini C.A.C. Sequeira, M.J. Hudson, Multifunctional Mesoporous Solids 1993 Kluwer Academic, Nato ASI Series Dordrecht 37
69. E.P. Barrett, L.G. Joyner, and P.P. Halenda J. Am. Chem. Soc. 73 1951 373
70. H.A. Benesi J. Am. Chem. Soc. 78 1956 5490
71. G. Alberti, U. Costantino, S. Alulli, and N. Tomassini J. Inorg. Nucl. Chem. 40 1978 1113
72. A. Clearfield K.D. Karlin, Progress in Inorganic Chemistry 1998 Wiley New York 371
73. G. Alberti G. Alberti, T. Bein, Solid State Supramolecular Chemistry of Comprehensive Supramolecular Chemistry, vol. 7 1996 Pergamon Press New York 151 Chapter 5
74. U. Costantino, M. Nocchetti, F. Marmottini, and R. Vivani Eur. J. Inorg. Chem. 1998 1447
75. X. Shi, J. Liu, and Q. Yang Inorg. Chem. 46 2007 7944
76. A. Hu, H.L. Ngo, and W. Lin J. Mol. Catal. A: Chem. 215 2004 177
77. G. Alberti, U. Costantino, J. Környei, and M.L.L. Giovagnotti React. Polym. 4 1985 1
78. K.S.W. Sing, D.H. Everett, R.A.W. Haul, L. Moscou, R.A. Pierotti, J. Rouquerol, and T. Siemieniewska Pure Appl. Chem. 57 1985 603