On the nature of the 'heterogeneous' catalyst: Nickel-on-charcoal

Journal of Organic Chemistry

Volumn 68, Issue 4, 2003, Pages 1177-1189

  Lipshutz, Bruce H ^a   Tasler, Stefan ^a   Chrisman, Will ^a   Spliethoff, Bernd ^b   Tesche, Bernd ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHARCOAL; ENERGY DISPERSIVE SPECTROSCOPY; FILTRATION; INDUCTIVELY COUPLED PLASMA; NICKEL; REACTION KINETICS; TRANSMISSION ELECTRON MICROSCOPY;

AROMATIC AMINATIONS;

CATALYSTS;

AROMATIC AMINE; CHARCOAL; NICKEL;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; FILTRATION; RECYCLING; SPECTROSCOPY; TRANSMISSION ELECTRON MICROSCOPY; X RAY ANALYSIS;

AMINATION; CATALYSIS; CHARCOAL; FILTRATION; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ELECTRON; MOLECULAR STRUCTURE; MORPHOLINES; NICKEL; OXIDATION-REDUCTION; SOLUTIONS;

EID: 0037458972     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020296m     Document Type: Article

References (111)

1. (a) Kharasch, M. S.; Tawney, P. O. J. Am. Chem. Soc. 1941, 63, 2308.
2. (b) Kharasch, M. S.; Fields, E. K. J. Am. Chem. Soc. 1941, 63, 2316.
3. (c) Kharasch, M. S.; Lambert, F. L.; Urry, W. H. J. Org. Chem. 1945, 10, 298.
4. (a) Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144.
5. (b) Cassar, L.; Giarrusso, A. Gazz. Chim. Ital. 1973, 103, 793.
6. (c) Cramer, R.; Coulson, D. R. J. Org. Chem. 1975, 40, 2267.
7. (d) Felkin, H.; Swierczewski, G. Tetrahedron 1975, 31, 2735.
8. (e) Kende, A. S.; Liebeskind, L. S.; Braitsch, D. M. Tetrahedron Lett. 1975, 3375.
9. (f) Pridgen, L. N. J. Heterocycl. Chem. 1975, 12, 443.
10. (g) Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.-I.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958.
11. (h) Zembayashi, M.; Tamao, K.; Yoshida, J.-I.; Kumada, M. Tetrahedron Lett. 1977, 4089.
12. (i) Yamamoto, T.; Hayashi, Y.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1978, 51, 2091.
13. (j) Takagi, K.; Hayama, N.; Okamoto, T. Chem. Lett. 1978, 191.
14. (k) Takagi, K.; Hayama, N.; Inokawa, S. Chem. Lett. 1979, 917.
15. (l) Ibuki, E.; Ozasa, S.; Fujioka, Y.; Okada, M.; Terada, K. Bull. Chem. Soc. Jpn. 1980, 53, 821.
16. (m) Kumada, M. Pure Appl. Chem. 1980, 52, 669.
17. (n) Semmelhack, M. F.; Helquist, P.; Jones, L. D.; Keller, L.; Mendelson, L.; Ryono, L. S.; Smith, J. G.; Stauffer, R. D. J. Am. Chem. Soc. 1981, 103, 6460.
18. (a) Tolman, C. A.; Seidel, W. C.; Gerlach, D. H. J. Am. Chem. Soc. 1972, 94, 2669.
19. (b) Tolman, C. A.; Seidel, W. C.; Gosser, L. W. J. Am. Chem. Soc. 1974, 96, 53.
20. (c) Stasko, A.; Tkac, A.; Prikryl, R.; Malik, L. J. Organomet. Chem. 1975, 92, 253.
21. (d) Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262.
22. (e) Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1977, 99, 2501.
23. (f) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1978, 100, 1634.
24. (g) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319.
25. (h) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 7547.
26. (i) Tsou, T. T.; Kochi, J. K. J. Org. Chem. 1980, 45, 1930.
27. (j) Kochi, J. K. Acc. Chem. Res. 1974, 7, 351.
28. (a) Heck reaction: Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320.
29. (b) Andersson, C.-M.; Hallberg, A. J. Org. Chem. 1987, 52, 3529.
30. (c) Hydrogenation: Klenke, B.; Gilbert, I. H. J. Org. Chem. 2001, 66, 2480.
31. (d) Savoia, D.; Trombini, C.; Umani-Ronchi, A.; Verardo, G. J. Chem. Soc., Chem. Commun. 1981, 540.
32. (e) Hydrodehalogenation: Jones, J. R.; Lockley, W. J. S.; Lu, S.-Y.; Thompson, S. P. Tetrahedron Lett. 2001, 42, 331.
33. (f) Reductive biaryl coupling: Mukhopadhyay, S.; Rothenberg, G.; Wiener, H.; Sasson, Y. Tetrahedron 1999, 55, 14763; and references therein.
34. (g) Venkatraman, S.; Li, C.-J. Org. Lett. 1999, 1, 1133.
35. (h) Stille coupling: Roth, G. P.; Farina, V.; Liebeskind, L. S.; Pena-Cabrera, E. Tetrahedron Lett. 1995, 36, 2191.
36. (i) Amidocarbonylation: Beller, M.; Moradi, W. A.; Eckert, M.; Neumann, H. Tetrahedron Lett. 1999, 40, 4523.
37. (j) Suzuki coupling: Dyer, U. C.; Shapland, P. D.; Tiffin, P. D. Tetrahedron Lett. 2001, 42, 1765; and references therein.
38. (k) Varma, R. S.; Naicker, K. P. Tetrahedron Lett. 1999, 40, 439.
39. (l) Stereoselective hydrogenation: Farkas, G.; Hegedus, L.; Tungler, A.; Mathe, T.; Figueiredo, J. L.; Freitas, M. J. Mol. Catal. A 2000, 153, 215.
40. (m) Aminations: Djakovitch, L.; Wagner, M.; Köhler, K. J. Organomet. Chem. 1999, 592, 225.
41. (n) Allylic substitution: Boldrini, G. P.; Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Organomet. Chem. 1984, 268, 97.
42. (o) Phosphination: Lai, C. W.; Kwong, F. Y.; Wang, Y.; Chan, K. S. Tetrahedron Lett. 2001, 42, 4883.
43. Bergbreiter, D. E.; Chen, B. J. Chem. Soc., Chem. Commun. 1983, 1238.
44. Augustine, R. L.; O'Leary, S. T. J. Mol. Catal. 1992, 72, 229.
45. For several polymer-bound Pd catalyzed reactions, see: Bergbreiter, D. E. Chem. Rev. 2002, 102, in press.
46. LeBlond, C. R.; Andrews, A. T.; Sun, Y.; Sowa, J. R., Jr. Org. Lett. 2001, 3, 1555; and references therein.
47. (a) Hydrogenation: Hill, F. N.; Selwood, P. W. J. Am. Chem. Soc. 1949, 71, 2522.
48. (b) Aika, K.-I.; Yamaguchi, T.; Onishi, T. Appl. Catal. 1986, 23, 129.
49. (c) Medina, F.; Salagre, P.; Sueiras, J. E. Appl. Catal. A 1993, 99, 115.
50. (d) Coq, B.; Figueras, F.; Geneste, P.; Moreau, C.; Moreau, P.; Warawdekar, M. J. Mol. Catal. 1993, 78, 211.
51. (e) Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1981, 46, 5344.
52. 2: Vannice, M. A. J. Catal. 1976, 44, 152.
53. (g) Vannice, M. A.; Garten, R. L. J. Catal. 1979, 56, 236.
54. (h) Decomposition of alkanes: Domingo-Garcia, M.; Fernandez-Morales, I.; Lopez-Garzon, F. J. Appl. Catal. A 1994, 112, 75.
55. (i) Otsuka, K.; Seino, T.; Kobayashi, S.; Takenaka, S. Chem. Lett. 1999, 1179.
56. (j) NO/CO: Mehandjiev, D.; Bekyarova, E.; Khristova, M. J. Colloid Interface Sci. 1997, 192, 440.
57. Gandia, L. M.; Montes, M. J. Catal. 1994, 145, 276.
58. Lipshutz, B. H. Adv. Synth. Catal. 2001, 343, 313.
59. Yakovlev, V. A.; Simagina, V. I.; Likholobov, V. A. React. Kinet. Catal. Lett. 1998, 65, 177.
60. Yakovlev, V. A.; Terskikh, V. V.; Simagina, V. I.; Likholobov, V. A. J. Mol. Catal. A 2000, 153, 231.
61. Styring, P.; Grindon, C.; Fisher, C. M. Catal. Lett. 2001, 77, 219. For a few other polymer-immobilized Ni reactions, see ref 7, 41, and Braca, G.; Di Girolamo, M.; Raspolli Galletti, A. M.; Sbrana, G.; Brunelli, M.; Bertolini, G. J. Mol. Catal. 1992, 74, 421.
62. Styring, P.; Grindon, C.; Fisher, C. M. Catal. Lett. 2001, 77, 219. For a few other polymer-immobilized Ni reactions, see ref 7, 41, and Braca, G.; Di Girolamo, M.; Raspolli Galletti, A. M.; Sbrana, G.; Brunelli, M.; Bertolini, G. J. Mol. Catal. 1992, 74, 421.
63. Lipshutz, B. H.; Blomgren, P. A. J. Am. Chem. Soc. 1999, 121, 5819.
64. Lipshutz, B. H.; Sclafani, J. A.; Blomgren, P. A. Tetrahedron 2000, 56, 2139.
65. Lipshutz, B. H.; Tomioka, T.; Blomgren, P. A.; Sclafani, J. A. Inorg. Chim. Acta 1999, 296, 164.
66. Lipshutz, B. H.; Ueda, H. Angew. Chem. 2000, 112, 4666; Angew. Chem., Int. Ed. 2000, 39, 4492.
67. Lipshutz, B. H.; Ueda, H. Angew. Chem. 2000, 112, 4666; Angew. Chem., Int. Ed. 2000, 39, 4492.
68. Lipshutz, B. H.; Tomioka, T.; Sato, K. Synlett 2001, 970.
69. (a) Horiuti, I.; Polanyi, M. Trans. Faraday Soc. 1934, 30, 1164.
70. (b) Augustine, R. L.; Yaghmaie, F.; Van Peppen, J. F. J. Org. Chem. 1984, 49, 1865.
71. (c) Ehwald, H.; Shestov, A. A.; Muzykantov, V. S. Catal. Lett. 1994, 25, 149.
72. (d) Ertl, G. Chem. Rec. 2001, 1, 33.
73. (e) Zaera, F. Acc. Chem. Res. 2002, 35, 129.
74. (a) Rebek, J., Jr. Tetrahedron 1979, 35, 723.
75. (b) Kagan, H. B.; Peyronel, J. F.; Yamagishi, T. In Advances in Chemistry - Inorganic Compounds With Unusual Properties II; King, R. B., Ed.; American Chemical Society: Washington, DC, 1979; Vol. 173, Chapter 6, pp 50-66.
76. Bergbreiter, D. E.; Chen, B.; Weatherford, D. J. Mol. Catal. 1992, 74, 409.
77. Davies, I. W.; Matty, L.; Hughes, D. L.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 10139.
78. Jayasree, S.; Seayad, A.; Chaudhari, R. V. J. Chem. Soc., Chem. Commun. 1999, 1067.
79. Biffis, A.; Zecca, M.; Basato, M. Eur. J. Inorg. Chem. 2001, 1131.
80. Zhao, F.; Bhanage, B. M.; Shirai, M.; Arai, M. Chem. Eur. J. 2000, 6, 843.
81. Lipshutz, B. H.; Tasler, S. Adv. Synth. Catal. 2001, 343, 327.
82. Anderson, J. R. Structure of Metallic Catalysts; Academic Press: New York, 1975, Chapter 2.12 and 4.
83. This result was in agreement with information supplied by the vendor of the charcoal used, concerning the impurities in their charcoal which can include up to 1% phosphates.
84. Bekyarova, E.; Mehandjiev, D. J. Colloid Interface Sci. 1996, 179, 509.
85. Parkes, G. D. Mellor's Modern Inorganic Chemistry; John Wiley & Sons Inc.: New York, 1967; p 938.
86. Stiles, A. B. Catalyst Supports and Supported Catalysts; Butterworth: Boston, 1987, Chapter 5.
87. Tasler, S.; Lipshutz, B. H. J. Org. Chem. 2002, 67, 1190.
88. (a) Amblard, J.; Platzer, O.; Ridard, J.; Belloni, J. J. Phys. Chem. 1992, 96, 2341.
89. (b) Khatouri, J.; Mostafavi, M.; Amblard, J.; Belloni, J. Chem. Phys. Lett. 1992, 191, 351.
90. (a) Segelstein, B. E.; Butler, T. W.; Chenard, B. L. J. Org. Chem. 1995, 60, 12.
91. (b) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441.
92. (c) Grushin, V. V. Organometallics 2000, 19, 1888.
93. (d) Kwong, F. Y.; Lai, C. W.; Tian, Y.; Chan, K. S. Tetrahedron Lett. 2000, 41, 10285.
94. (e) Kwong, F. Y.; Chan, K. S. Organometallics 2001, 20, 2570.
95. Inductively Coupled Plasma Mass Spectrometry; Montaser, A., Ed.; Wiley-VCH: New York, 1998.
96. For further applications of this method, see work cited in ref 25.
97. 'Adsorption' is used here in a broad sense, including the trapping of substrates within the martix.
98. Vol'pin, M. E.; Novikov, Y. N.; Lapkina, N. D.; Kasatochkin, V. I.; Struchkov, Y. T.; Kazakov, M. E.; Stukan, R. A.; Povitskij, V. A.; Karimov, Y. S.; Zvarikina, A. V. J. Am. Chem. Soc. 1975, 97, 3366.
99. Fontaine, F.-G.; Zargarian, D. Organametallics 2002, 21, 401.
100. Pittman, C. U., Jr.; Smith, L. R. J. Am. Chem. Soc. 1975, 97, 341.
101. sol concentrations reached a maximum after ca. 1 h reaction time, see ref 26; in the case of Ni/C, however, a trace level of bleed seems to occur in minutes.
102. 28,30,32
103. sol, most of which is 'stored' within the support.
104. (a) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
105. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95.
106. (a) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264.
107. (b) Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6054.
108. (c) Takezawa, T.; Kusano, T. Nippon Kagaku Kaishi 1981, 1129; Chem. Abstr. 1981, 95, 203442e.
109. (c) Takezawa, T.; Kusano, T. Nippon Kagaku Kaishi 1981, 1129; Chem. Abstr. 1981, 95, 203442e.
110. (d) Miki, Y.; Sugimoto, Y. Busshitsu Kogaku Kogyo Gijutsu Kenkyusho Hokoku 1998, 6, 31; Chem. Abstr. 1998, 128, 204636h.
111. (d) Miki, Y.; Sugimoto, Y. Busshitsu Kogaku Kogyo Gijutsu Kenkyusho Hokoku 1998, 6, 31; Chem. Abstr. 1998, 128, 204636h.