Critical assessment of the efficiency of chitosan biohydrogel beads as recyclable and heterogeneous organocatalyst for C–C bond formation

Green Chemistry

Volumn 14, Issue 2, 2012, Pages 378-392

  Kühbeck, Dennis ^a   Saidulu, G ^b   Reddy, K Rajender ^b   Díaz, David Díaz ^a,c  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^c CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84857173816     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c1gc15925a     Document Type: Article

References (82)

1. R. Höfer J. Bigorra Green Chem. 2007 9 203-212.
2. M. Elnashar (Ed.), Biopolymers, InTech, 2010.
3. 11 tons per year, see: K. Kurita Mar. Biotechnol. 2006 8 203-226.
4. M. N. V R. Kumar React. Funct. Polym. 2000 46 1-27.
5. G. A. F. Roberts, Chitin chemistry, 1st Edition, Macmillan, London, UK, 1992.
6. K. Tharanathan Crit. Rev. Food Sci. Nutr. 2003 43 61-87.
7. K. C. Gupta M. N. V. R. Kumar J. Appl. Polym. Sci. 2000 76 672-683.
8. C. Qin H. Li Q. Xiao Y. Liu J. Zhu Y. Du Carbohydr. Polym. 2006 63 367-374.
9. A. V. Il’ina V. P. Varlamov Appl. Biochem. Microbiol. 2003 39 239-243.
10. Y. Shchipunov S. Sarin, Il K. C.-S. Ha Green Chem. 2010 12 1187-1195 and references therein.
11. K. Kurita K. Tomita T. Tada S. Ishii S. Nishimura K. Shimoda J. Polym. Sci., Part A: Polym. Chem. 1993 31 485-491.
12. M. R. Kasaai Carbohydr. Polym. 2008 71 497-508.
13. H. Honarkar M. Barikani Monatsh. Chem. 2009 140 1403-1420.
14. D. J. Macquarrie Ind. Eng. Chem. Res. 2005 44 8499-8520.
15. E. Guibal Prog. Polym. Sci. 2005 30 71-109.
16. Y. Liu C. Peng S. Linyong Y. Fang Radiat. Phys. Chem. 2007 76 1165-1168.
17. H. Zhang W. Zhao J. Zou Y. Liu R. Li Y. Cui Chirality 2009 21 492-496 and references therein.
18. Y. Cui H. Zhang R. Li Y. Liu C. Xu Chinese J. Org. Chem. 2010 30 707-712.
19. L. R. MacGillivray J. L. Reid J. A. Ripmeester J. Am. Chem. Soc. 2000 122 7817-7818.
20. F. Quignard R. Valentin F. Di Renzo New J. Chem. 2008 32 1300-1310.
21. R. Valentin K. Molvinger F. Quignard D. Brunel New J. Chem. 2003 27 1690-1692.
22. A. Ricci L. Bernardi C. Gioia S. Vierucci M. Robitzer F. Quignard Chem. Commun. 2010 46 6288-6298.
23. N. Sudheesh S. K. Sharma R. S. Shukla J. Mol. Catal. A: Chem. 2010 321 77-82.
24. K. R. Reddy K. Rajgopal C. U. Maheswari M. L. Kantam New J. Chem. 2006 30 1549-1552.
25. F. Rodríguez-Llansola J. F. Miravet B. Escuder Chem. Commun. 2009 7303-7305.
26. Rodríguez-Llansola B. Escuder J. F. Miravet J. Am. Chem. Soc. 2009 131 11478-11484.
27. F. Rodríguez-Llansola J. F. Miravet B. Escuder Chem.–Eur. J. 2010 16 8480-8486.
28. See ESI for additional details G. D. Parfitt, C. H. Rochester, in Adsorption from Solution at the Solid/Liquid Interface. Academic Press, Inc.: Orlando, FL 1983, 9-13.
29. H. Corcoran D.-J. Sung S. Banerjee Ind. Eng. Chem. Res. 2001 40 152-155.
30. Sudipta Chatterjee Min W. Lee Seung H. Woo Chem. Eng. J. 2009 155 254-259 and references therein.
31. M. Shiriu S. Xintao U. Florian S. Michael B. Dianzhou K. Thomas Int. J. Pharm. 2004 281 45-54.
32. L. S. Guinesi É. T. G. Cavalheiro Thermochim. Acta 2006 444 128-133.
33. K. M. Delak N. Sahai Chem. Mater. 2005 17 3221-3227.
34. F. Rodríguez-Llansola B. Escuder J. F. Miravet Org. Biomol. Chem. 2009 7 3091-3094.
35. The term “no conversion” has been generally adopted during the entire manuscript to indicate product formation below 1% as detected by NMR analysis.
36. Such low reaction conversion was also observed if the CSHB were first stirred in the presence of acetone (30 min) before addition of the aldehyde.
37. In general, aldol reactions may be catalyzed either by a base or an acid, where the nucleophile is an enolate anion or enol, respectively. In the latter case, catalytic protonation of the carbonyl oxygen increases the electrophilicity of the carbonyl carbon just enough so that it can be attacked by the enol, and promote the dehydration of the aldol product, as water is a good leaving group. Nevertheless, it is well known that aldol reactions proceed more efficiently under basic conditions where dehydration rarely takes place during the reaction since hydroxide is a poor leaving group.
38. 2 and Ag(0), which could be further quantified by AAS.
39. L.-W. Xu J. Luo Y. Lu Chem. Commun. 2009 1807-1821 and references therein.
40. D. D. Díaz D. Kühbeck R. J. Koopmans Chem. Soc. Rev. 2011 40 427-448.
41. K. Sakthivel W. Notz T. Bui C. F. Barbas III J. Am. Chem. Soc. 2001 123 5260-5267.
42. M. Amedjkouh Tetrahedron: Asymmetry 2005 16 1411-1414.
43. L. Chao-Jun Chem. Rev. 2005 105 3095-3165 and references therein.
44. Y. Hayashi T. Sumiya J. Takahashi H. Gotoh T. Urushima M. Shoji Angew. Chem., Int. Ed. 2006 45 958-961.
45. Y. Hayashi Angew. Chem., Int. Ed. 2006 45 8103-8104 and references therein.
46. D. Gryko W. J. Saletra Org. Biomol. Chem. 2007 5 2148-2153.
47. 2O, 48 h, RT.
48. M. Chtchigrovsky A. Primo P. Gonzalez K. Molvinger M. Robitzer F. Quignard F. Taran Angew. Chem. 2009 121 6030-6034.
49. A. Primo F. Quignard Chem. Commun. 2010 46 5593-5595.
50. 1H NMR analysis of the extracts did not show any signal corresponding to the reaction product, but only signals of the starting aldehyde (ca. 8 mol%).
51. N. T. S. Phan C. W. Jones J. Mol. Catal. A: Chem. 2006 256 123-131.
52. G. Jenner Tetrahedron Lett. 2001 42 243-245.
53. M. L. Deb P. J. Bhuyan Tetrahedron Lett. 2005 46 6453-6456.
54. J. A. Gladysz Pure Appl. Chem. 2001 73 1319-1324.
55. T.-Y. Hsien G. L. Rorrer Ind. Eng. Chem. Res. 1997 36 3631-3638.
56. K. A. Utting D. J. Macquarrie New J. Chem. 2000 24 591-595.
57. B. Falk S. Garramone S. Shivkumar Mater. Lett. 2004 58 3261-3265.
58. T. Vincent F. Peirano E. Guibal J. Appl. Polym. Sci. 2004 94 1634-42 and references therein.
59. F. A. Luzzio Tetrahedron 2001 57 915-945 and references therein.
60. K. K. Sharma A. V. Biradar T. Asefa ChemCatChem 2010 2 61-66 and references therein.
61. L. Kurti, B. Czako, Strategic Applications of Named Reactions in Organic Synthesis. Burlington, MA: Elsevier Academic Press. pp. 202-203, 2005.
62. Additional experiments have shown that 4 h is enough to achieve practically full conversion in DMSO.
63. A. Heeres F. F. Spoelma H. A. van Doren K. F. Gotlieb I. P. Bleeker R. M. Kellogg Carbohydr. Polym. 2000 42 33-43.
64. V. G. Kiselev N. P. Gritsan Khim. Fiz. 2006 25 54-61.
65. P. Politzer J. M. Seminario A. C. Zacarías Mol. Phys. 1996 89 1511-1520.
66. S. Zeman T. Atalar Z. Friedl X.-H. Ju Cent. Eur. J. Energ. Mater. 2009 6 119-133.
67. C. Capello U. Fischer K. Hungerbühler Green Chem. 2007 9 927-934.
68. P. J. Dunn D. A. Perry Green Chem. 2008 10 31-36.
69. Richard K. Henderson Concepción Jiménez-González David J. C. Constable Sarah R. Alston Graham G. A. Inglis Gail Fisher James Sherwood Steve P. Binks Alan D. Curzons Green Chem. 2011 13 854-862.
70. P. G. Jessop Green Chem. 2011 13 6 1391.
71. M. Gruber-Khadjawi T. Purkarthofer W. Skranc H. Griengla Adv. Synth. Catal. 2007 349 1445-1450.
72. T. Purkarthofer K. Gruber M. Gruber-Khadjawi K. Waich W. Skranc D. Mink H. Griengl Angew. Chem. Int. Ed. 2006 45 3454-3456.
73. G. Blay L. R. Domingo V. Hernández-Olmos J. R. Pedro Chem. Eur. J. 2008 14 4725-4730.
74. E. Busto V. Gotor-Fernández V. Gotor Org. Process Res. Dev. 2011 15 236-240.
75. H. M. Al-Matar K. D. Khalil H. Meier H. Kolshorn M. H. Elnagdi Arkivoc 2008 288-301.
76. R. Pedrosa J. M. Andrés R. Manzano P. Rodríguez Eur. J. Org. Chem. 2010 5310-5319.
77. B. S. Rane M. A. Kazi S. M. Bagul D. P. Shelar R. B. Toche M. N. Jachak J. Fluoresc. 2010 20 415-420.
78. J. S. Yadav B. V. S. Reddy A. K. Basak B. Visali A. V. Narsaiah K. Nagaiah Eur. J. Org. Chem. 2004 546-551.
79. Y. Luo L. Ma H. Zheng L. Chen R. Li C. He S. Yang X. Ye Z. Chen Z. Li Y. Gao J. Han G. He L. Yang Y. Wei J. Med. Chem. 2010 53 273-281.
80. T. S. Jin R.-Q. Zhao M. Li Y. Zhao T.-S. Li Arkivoc 2006 53-58.
81. G. Lai F. Guo Y. Zheng Y. Fang H. Song K. Xu S. Wang Z. Zha Z. Wang Chem. Eur. J. 2011 17 1114-1117.
82. For the description of the dehydrated product, see: J.-M. Liu X. Wang Z.-M. Ge Q. Sun T.-M. Cheng R.-T. Li Tetrahedron 2011 67 636-640.