Heck reaction catalyzed by nanosized palladium on chitosan in ionic liquids

Organometallics

Volumn 23, Issue 22, 2004, Pages 5154-5158

  Calò, Vincenzo ^a   Nacci, Angelo ^a   Monopoli, Antonio ^a   Fornaro, Antonio ^a   Sabbatini, Luigia ^a   Cioffi, Nicola ^a   Ditaranto, Nicoletta ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; CATALYSIS; COLLOIDS; ORGANIC SOLVENTS; OXIDATION; PALLADIUM; TRANSMISSION ELECTRON MICROSCOPY;

CHITOSANS; HECK REACTIONS; NANOCOLLOIDS; NEUTRALIZATION;

REACTION KINETICS;

EID: 8344281468     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049586e     Document Type: Article

References (113)

1. (a) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518.
2. (b) Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1996.
3. Negishi, E.-I., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley: New York, 2002.
4. Reviews: (a) de Meijer, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427. (d) Genet, J. P.; Savignac, M. J. J. Organomet. Chem. 1999, 576, 305. (e) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. (f) Withcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449-7476.
5. Reviews: (a) de Meijer, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427. (d) Genet, J. P.; Savignac, M. J. J. Organomet. Chem. 1999, 576, 305. (e) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. (f) Withcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449-7476.
6. Reviews: (a) de Meijer, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427. (d) Genet, J. P.; Savignac, M. J. J. Organomet. Chem. 1999, 576, 305. (e) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. (f) Withcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449-7476.
7. Reviews: (a) de Meijer, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427. (d) Genet, J. P.; Savignac, M. J. J. Organomet. Chem. 1999, 576, 305. (e) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. (f) Withcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449-7476.
8. Reviews: (a) de Meijer, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427. (d) Genet, J. P.; Savignac, M. J. J. Organomet. Chem. 1999, 576, 305. (e) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. (f) Withcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449-7476.
9. Reviews: (a) de Meijer, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427. (d) Genet, J. P.; Savignac, M. J. J. Organomet. Chem. 1999, 576, 305. (e) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. (f) Withcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449-7476.
10. For a mechanistic study on the Heck reaction see: Amatore, C.; Jutand, A. J. Organomet. Chem. 1999, 576, 254.
11. (a) Herrmann, W. A.; Brossmer, C.; Ofele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844.
12. (b) Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Riermeier, T. H.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357.
13. (c) Böhm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2001, 7, 4191.
14. (a) Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031-3033.
15. (b) Viciu, M. S.; Kelly, R. A., III; Stevens, E. D.; Naud, F.; Studer, M.; Nolan, S. P. Org. Lett. 2003, 5, 1479-1482.
16. (c) For a Pdbenzothiazole carbene complex see: Calò, V.; Nacci, A.; Lopez, L.; Mannarini, N. Tetrahedron Lett. 2000, 41, 8973-8976.
17. (d) For general reviews see: Herrmann, W. A.; Böhm, V. P. W. Angew. Chem., Int. Ed. 1997, 36, 2162-2187.
18. (e) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 2000, 600, 12-22.
19. (f) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
20. (g) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
21. (a) Andersson, C.-M.; Karabelas, K.; Hallberg, A. J. Org. Chem. 1985, 50, 3891-3895.
22. (b) Andersson, C.-M.; Hallberg, A. J. Org. Chem. 1987, 52, 3529-3536.
23. (c) Andersson, C.-M.; Hallberg, A. J. Org. Chem. 1988, 53, 235-239.
24. (d) Yi, P.; Zhuangyu, Z.; Hongwen, H. J. Mol. Catal. 1990, 62, 297-306.
25. (e) Wang, P. W.; Fox, M. A. J. Org. Chem. 1994, 59, 5358-5364.
26. (f) Kiviaho, J.; Hanaoka, T.; Kubota, Y.; Sugi, Y. J. Mol. Catal. A: Chem. 1995, 101, 25-31.
27. (g) Villemin, D.; Jaffres, P. A.; Nechab, B.; Courivaud, F. Tetrahedron Lett. 1997, 38, 6581-6584.
28. (h) Bhanage, B. M.; Shirai, M.; Arai, M. J. Mol. Catal. A: Chem. 1999, 145, 69-74.
29. Varma, R. S.; Naicker, K. P.; Liesen, P. J. Tetrahedron Lett. 1999, 40, 439-442.
30. (j) Schwarz, J.; Böhm, V. P. W.; Gardiner, M. G.; Grosche, M.; Herrmann, W. A.; Hieringer, W.; Raudaschl-Sieber, G. Chem. Eur. J. 2000, 6, 1773-1780.
31. (k) Akyama, R.; Kobayashi, S. J. Am. Chem. Soc. 2002, 125, 3412-3413.
32. Doi, T.; Fujimoto, N.; Watanabe, J.; Takahashi, T. Tetrahedron Lett. 2003, 44, 2161-2165.
33. Scott, R. W.; Datye, A. K.; Crooks, R. M. J. Am. Chem. Soc. 2003, 125, 3708-3709.
34. (n) Dahan, A.; Portnoy, M. Org. Lett. 2003, 5, 1197-1200.
35. (o) Zhao, S. F.; Zhou, R. X.; Zheng, X. M. J. Mol. Catal. A: Chem. 2004, 211, 139-142. For a review see: Benaglia, M.; Puglisi, A.; Cozzi, F. Chem. Rev. 2003, 703, 3401-3429.
36. (o) Zhao, S. F.; Zhou, R. X.; Zheng, X. M. J. Mol. Catal. A: Chem. 2004, 211, 139-142. For a review see: Benaglia, M.; Puglisi, A.; Cozzi, F. Chem. Rev. 2003, 703, 3401-3429.
37. (a) Choudary, B. M.; Sarma, R. M.; Rao, K. K. Tetrahedron 1992, 48, 719-726.
38. (b) Augustine, R. L.; O'Leary, S. T. J. Mol. Catal. A: Chem. 1995, 95, 277-285.
39. (c) Beller, M.; Kühlein, K. Synlett 1995, 441-442.
40. (d) Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Lett. 1995, 36, 4567-4570.
41. (e) Wali, A.; Pillai, S. M.; Kaushik, V. K.; Satish, S. Appl. Catal. A: Gen. 1996, 735, 83-93.
42. (f) Shmidt, A. F.; Vladimirova, T. A.; Shmidt, E. Y. Kinet. Katal. 1997, 38, 245-250.
43. (g) Shmidt, A. F.; Khalaika, A.; Nindakova, L. O.; Shmidt, E. Y. Kinet. Katal. 1998, 39, 200-206.
44. (h) Zhao, F.; Bhanage, B. M.; Shirai, M.; Arai, M. Chem. Eur. J. 2000, 6, 843-848.
45. Wagner, M.; Köhler, K.; Djakovitch, L.; Weinkauf, S.; Hagen, V.; Muhler, M. Top. Catal. 2000, 13, 319-326.
46. (j) Djakovitch, L.; Köhler, K. J. Am. Chem. Soc. 2001, 123, 5990-5999.
47. (k) Mori, K.; Yamaguchi, K.; Hara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2002, 124, 11572-11573.
48. Yang, H.; Zhang, G.; Hong, X.; Zhu, Y. J. Mol. Catal. A: Chem. 2004, 210, 143-148. For Pd/C-catalyzed Heck reactions see: Brase, S.; Waegell, B.; de Mejere, A. Synthesis 1998, 148-152 and references therein.
49. Yang, H.; Zhang, G.; Hong, X.; Zhu, Y. J. Mol. Catal. A: Chem. 2004, 210, 143-148. For Pd/C-catalyzed Heck reactions see: Brase, S.; Waegell, B.; de Mejere, A. Synthesis 1998, 148-152 and references therein.
50. (a) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000.
51. (b) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. N.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127-14136.
52. (a) Reetz, M. T.; Lohmer, G. Chem. Commun. 1996, 1921-1922.
53. (b) Beller, M.; Fisher, H.; Kühlein, K.; Reisinger, C.-P.; Herrmann, W. A. J. Organomet. Chem. 1996, 520, 257-259.
54. (c) Reetz, M. T.; Breinbauer, R.; Wanninger, K. Tetrahedron Lett. 1996, 37, 4499-4502.
55. (d) Klingelhofer, S.; Heitz, W.; Greiner, A.; Oestreich, S.; Forster, S.; Antonietti, M. J. Am. Chem. Soc. 1997, 119, 10116-10120.
56. (e) Reetz, M. T.; Westermann, E. Angew. Chem., Int. Ed. 2000, 39, 165-168.
57. (f) Moreno-Manas, M.; Pleixsats, R.; Villarroya, S. Organometallics 2001, 20, 4524-4528.
58. (g) Desmukh, R. R.; Rajagopal, R.; Srinivasan, K. V. Chem. Commun. 2001, 1544-1545.
59. (h) Galow, T. H.; Drechsler, U.; Hanson, J. A.; Rotello, V. M. Chem. Commun. 2002, 1076-1077.
60. Rocaboy, C.; Gladysz, J. A. Org. Lett. 2002, 4, 1993-1996.
61. (j) de Vries, A. H. M.; Mulders, J. M. C. A.; Mommers, J. H. M.; Henderickx, U. J. W.; de Vries, J. G. Org. Lett 2003, 5, 3285-3288.
62. (k) Le Bars, J.; Specht, U.; Bradley, J. S.; Blackmond, D. G. Langmuir 1999, 15, 7621-7625.
63. Kim, S.-W.; Park, J.; Jang, Y.; Chung, Y.; Hwang, S.; Hyeon, T. Nano Lett. 2003, 3, 1289-1291.
64. Gopidas, K. R.; Whitesell, J. K.; Fox, M. A. Nano Lett. 2003, 3, 1757-1760.
65. (n) Consorti, C. S.; Zanini, M. L.; Leal, S.; Ebeling, G.; Dupont, J. Org. Lett. 2003, 5, 983-986.
66. (o) Yuranov, I.; Moeckli, P.; Suvarova, E.; Buffat, P.; Kiwi-Minsker, L.; Renken, A. J. Mol. Catal. A: Chem. 2003, 192, 239-251.
67. (p) Bergbreiter, D. E.; Li, J. Chem. Commun. 2004, 42-43.
68. (q) For a review see: Moreno-Manas, M.; Pleixsats, R. Acc. Chem. Res. 2003, 36, 638-643 and references therein.
69. For the stabilization of nanoclusters see: (a) Reetz, M. T.; Helbig, W.; Quaiser, S. A.; Stimming, U.; Breuer, N.; Vogel, R. Science 1995, 267, 367-369. (b) Aiken, J. D.; Finke, R. G. J. Mol. Catal. A: Chem. 1999, 145, 1-44. (c) Ozkar, S.; Finke, R. G. J. Am. Chem. Soc. 2002, 124, 5796-5810.
70. For the stabilization of nanoclusters see: (a) Reetz, M. T.; Helbig, W.; Quaiser, S. A.; Stimming, U.; Breuer, N.; Vogel, R. Science 1995, 267, 367-369. (b) Aiken, J. D.; Finke, R. G. J. Mol. Catal. A: Chem. 1999, 145, 1-44. (c) Ozkar, S.; Finke, R. G. J. Am. Chem. Soc. 2002, 124, 5796-5810.
71. For the stabilization of nanoclusters see: (a) Reetz, M. T.; Helbig, W.; Quaiser, S. A.; Stimming, U.; Breuer, N.; Vogel, R. Science 1995, 267, 367-369. (b) Aiken, J. D.; Finke, R. G. J. Mol. Catal. A: Chem. 1999, 145, 1-44. (c) Ozkar, S.; Finke, R. G. J. Am. Chem. Soc. 2002, 124, 5796-5810.
72. Reviews: (a) Gordon, C. M. Appl. Catal. A: Gen. 2001, 222, 101-117. (b) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 182-183, 419-437. (c) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692. (d) Holbrey, J. D.; Seddon, K. R. Clean Prod. Processes 1999, 1, 223-1346. (e) Welton, T. Chem. Rev. 1999, 99, 2071-2084. (f) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
73. Reviews: (a) Gordon, C. M. Appl. Catal. A: Gen. 2001, 222, 101-117. (b) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 182-183, 419-437. (c) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692. (d) Holbrey, J. D.; Seddon, K. R. Clean Prod. Processes 1999, 1, 223-1346. (e) Welton, T. Chem. Rev. 1999, 99, 2071-2084. (f) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
74. Reviews: (a) Gordon, C. M. Appl. Catal. A: Gen. 2001, 222, 101-117. (b) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 182-183, 419-437. (c) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692. (d) Holbrey, J. D.; Seddon, K. R. Clean Prod. Processes 1999, 1, 223-1346. (e) Welton, T. Chem. Rev. 1999, 99, 2071-2084. (f) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
75. Reviews: (a) Gordon, C. M. Appl. Catal. A: Gen. 2001, 222, 101-117. (b) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 182-183, 419-437. (c) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692. (d) Holbrey, J. D.; Seddon, K. R. Clean Prod. Processes 1999, 1, 223-1346. (e) Welton, T. Chem. Rev. 1999, 99, 2071-2084. (f) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
76. Reviews: (a) Gordon, C. M. Appl. Catal. A: Gen. 2001, 222, 101-117. (b) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 182-183, 419-437. (c) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692. (d) Holbrey, J. D.; Seddon, K. R. Clean Prod. Processes 1999, 1, 223-1346. (e) Welton, T. Chem. Rev. 1999, 99, 2071-2084. (f) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
77. Reviews: (a) Gordon, C. M. Appl. Catal. A: Gen. 2001, 222, 101-117. (b) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 182-183, 419-437. (c) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692. (d) Holbrey, J. D.; Seddon, K. R. Clean Prod. Processes 1999, 1, 223-1346. (e) Welton, T. Chem. Rev. 1999, 99, 2071-2084. (f) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
78. (a) Hagiwara, H.; Shimizu, Y.; Hoshi, T.; Suzuki, T.; Ando, M.; Ohkubo, K.; Yokoyama, C. Tetrahedron Lett. 2001, 42, 4349-4351.
79. (b) Xu, L.; Chen, W.; Xiao, J. Organometallics 2000, 19, 1123-1127.
80. (c) Zao, H.; Malhotra, S. V. Aldrichim. Acta 2002, 35, 75-83.
81. (d) Dupont, J.; Fonseca, G. S.; Umpierre, A. P.; Fichtner, P. F. P.; Teixseira, S. R. J. Am. Chem. Soc. 2002, 124, 4228-4229.
82. (e) Larhed, M.; Hallberg, A. J. Org. Chem. 2002, 67, 6243-6246.
83. (f) Zou, G.; Wang, Z.; Zhu, J.; Tang, J.; He, M. J. J. Mol. Catal. A: Chem. 2003, 206, 193-198.
84. (g) Park, S. B.; Alper, H. Org. Lett. 2003, 5, 3209-3212.
85. (h) Handy, S. T.; Okello, M.; Dickenson, G. Org. Lett. 2003, 5, 2513-2515.
86. (a) Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997-1000.
87. (b) Herrmann, W. A.; Böhm, V. P. W. Chem. Eur. J. 2000, 6, 1017-1025.
88. (c) Vallin, K. S. A.; Emilsson, F.; Larhed, M.; Hallberg, A. J. Org. Chem. 2002, 67, 6243-6246.
89. (d) Xu, L.; Chen, W.; Xiao, J. Org. Lett. 2003, 5, 295-297.
90. For the Heck reaction in tetraalkylammonium salts as solvents see: (a) Jeffery, T.; David, M. Tetrahedron Lett. 1998, 39, 5751-5754. (b) Kaufmann, D. E.; Nourozian, M.; Henze, H. Synlett 1996, 1091-1092. (c) Bouquillon, S.; Ganchegui, B.; Strine, B.; Muzart, J. J. Organomet. Chem. 2001, 634, 153-156. (d) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Synlett 2002, 439-442. (e) Reference 6a.
91. For the Heck reaction in tetraalkylammonium salts as solvents see: (a) Jeffery, T.; David, M. Tetrahedron Lett. 1998, 39, 5751-5754. (b) Kaufmann, D. E.; Nourozian, M.; Henze, H. Synlett 1996, 1091-1092. (c) Bouquillon, S.; Ganchegui, B.; Strine, B.; Muzart, J. J. Organomet. Chem. 2001, 634, 153-156. (d) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Synlett 2002, 439-442. (e) Reference 6a.
92. For the Heck reaction in tetraalkylammonium salts as solvents see: (a) Jeffery, T.; David, M. Tetrahedron Lett. 1998, 39, 5751-5754. (b) Kaufmann, D. E.; Nourozian, M.; Henze, H. Synlett 1996, 1091-1092. (c) Bouquillon, S.; Ganchegui, B.; Strine, B.; Muzart, J. J. Organomet. Chem. 2001, 634, 153-156. (d) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Synlett 2002, 439-442. (e) Reference 6a.
93. For the Heck reaction in tetraalkylammonium salts as solvents see: (a) Jeffery, T.; David, M. Tetrahedron Lett. 1998, 39, 5751-5754. (b) Kaufmann, D. E.; Nourozian, M.; Henze, H. Synlett 1996, 1091-1092. (c) Bouquillon, S.; Ganchegui, B.; Strine, B.; Muzart, J. J. Organomet. Chem. 2001, 634, 153-156. (d) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Synlett 2002, 439-442. (e) Reference 6a.
94. For the Heck reaction in tetraalkylammonium salts as solvents see: (a) Jeffery, T.; David, M. Tetrahedron Lett. 1998, 39, 5751-5754. (b) Kaufmann, D. E.; Nourozian, M.; Henze, H. Synlett 1996, 1091-1092. (c) Bouquillon, S.; Ganchegui, B.; Strine, B.; Muzart, J. J. Organomet. Chem. 2001, 634, 153-156. (d) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Synlett 2002, 439-442. (e) Reference 6a.
95. (a) Calò, V.; Nacci, A.; Lopez, L.; Napola, A. Tetrahedron Lett. 2001, 42, 4701-4703.
96. (b) Calò, V.; Nacci, A.; Monopoli, A.; Lopez, L.; di Cosmo, A. Tetrahedron 2001, 57, 6071-6077.
97. (c) Calò, V.; Nacci, A.; Monopoli, A.; Spinelli, M. Eur. J. Org. Chem. 2003, 1382-1385.
98. Calò, V.; Nacci, A.; Monopoli, A.; Laera, S.; Cioffi, N. J. Org. Chem. 2003, 68, 2929-2933.
99. Calò, V.; Nacci, A.; Monopoli, A.; Detomaso, A.; Iliade, P. Organometallics 2003, 22, 4193-4197.
100. Reetz, M. T.; Maase, M. Adv. Mater. 1999, 11, 773-777.
101. Domare, A.; Roberts, G. A. F. Advances in Chitin Science; André, J., Ed.: National Taiwan Ocean University: Keelung, Taiwan, 1998.
102. (a) Quignard, F.; Choplin, A.; Domard, A. Langmuir 2000, 16, 9106-9108.
103. (b) Huang, A.; Liu, Y.; Hua, J. J. Appl. Polym. Sci. 2002, 85, 989-994.
104. (c) Vincent, T.; Guibal, E. Ind. Eng. Chem. Res. 2002, 41, 5158-5164.
105. (d) Vincent, T.; Guibal, E. Langmuir 2003, 19, 8475-8483.
106. (e) Zhang, J.; Xia, C.-G. J. Mol. Catal. A: Chem. 2003, 206, 59-65.
107. (f) Adlim, M.; Abu Bakar, M.; Liew, K. Y.; Ismail, J. J. Mol. Catal. A: Chem. 2004, 212, 141-149.
108. For electrochemically prepared Pd nanocolloids see: (a) Reetz, M. T.; Winter, M.; Breinbauer, R.; Thurn-Albrecht, T.; Vogel, W. Chem. Eur. J. 2001, 7, 1084-1094. (b) Reetz, M. T.; Helbig, W. J. Am. Chem. Soc. 1994, 116, 7401. (c) Reetz, M. T.; Helbig, W.; Quaiser, S. A.; Stimming, U.; Breuer, N.; Vogel, R. Science 1995, 267, 367. (d) Cioffi, N.; Losito, I.; Torsi, L.; Sabbatini, L.; Zambonin, P. G.; Bleve-Zacheo, T. Electrochim. Acta 2001, 46, 4205.
109. For electrochemically prepared Pd nanocolloids see: (a) Reetz, M. T.; Winter, M.; Breinbauer, R.; Thurn-Albrecht, T.; Vogel, W. Chem. Eur. J. 2001, 7, 1084-1094. (b) Reetz, M. T.; Helbig, W. J. Am. Chem. Soc. 1994, 116, 7401. (c) Reetz, M. T.; Helbig, W.; Quaiser, S. A.; Stimming, U.; Breuer, N.; Vogel, R. Science 1995, 267, 367. (d) Cioffi, N.; Losito, I.; Torsi, L.; Sabbatini, L.; Zambonin, P. G.; Bleve-Zacheo, T. Electrochim. Acta 2001, 46, 4205.
110. For electrochemically prepared Pd nanocolloids see: (a) Reetz, M. T.; Winter, M.; Breinbauer, R.; Thurn-Albrecht, T.; Vogel, W. Chem. Eur. J. 2001, 7, 1084-1094. (b) Reetz, M. T.; Helbig, W. J. Am. Chem. Soc. 1994, 116, 7401. (c) Reetz, M. T.; Helbig, W.; Quaiser, S. A.; Stimming, U.; Breuer, N.; Vogel, R. Science 1995, 267, 367. (d) Cioffi, N.; Losito, I.; Torsi, L.; Sabbatini, L.; Zambonin, P. G.; Bleve-Zacheo, T. Electrochim. Acta 2001, 46, 4205.
111. For electrochemically prepared Pd nanocolloids see: (a) Reetz, M. T.; Winter, M.; Breinbauer, R.; Thurn-Albrecht, T.; Vogel, W. Chem. Eur. J. 2001, 7, 1084-1094. (b) Reetz, M. T.; Helbig, W. J. Am. Chem. Soc. 1994, 116, 7401. (c) Reetz, M. T.; Helbig, W.; Quaiser, S. A.; Stimming, U.; Breuer, N.; Vogel, R. Science 1995, 267, 367. (d) Cioffi, N.; Losito, I.; Torsi, L.; Sabbatini, L.; Zambonin, P. G.; Bleve-Zacheo, T. Electrochim. Acta 2001, 46, 4205.
112. Neghishi, E.-I.; Takahashi, T.; Akiyoshi, K. Chem. Commun. 1986, 1338-1339.
113. b value of acetate anion in TBAB. This value cannot be the same as that measured in water. This would not be surprising, since in this solvent the anion, being poorly solvated, should be a stronger base than in water.