Amination of benzylic C-H bonds by arylazides catalyzed by CoII-porphyrin complexes: A synthetic and mechanistic study

Chemistry - A European Journal

Volumn 9, Issue 1, 2003, Pages 249-259

  Ragaini, Fabio ^a   Penoni, Andrea ^a   Gallo, Emma ^a   Tollari, Stefano ^b   Li Gotti, Claudia ^a   Lapadula, Marta ^a   Mangioni, Enrica ^a   Cenini, Sergio ^a  

^a CNR   (Italy)

^b Dipto Sci Chimiche Fisiche M   (Italy)

Author keywords

Amination; Azides C H activation; Cobalt porphyrinoids

Indexed keywords

BENZENE; CATALYSIS; CHEMICAL BONDS; PORPHYRINS; REACTION KINETICS; TOLUENE;

ISOTOPIC EFFECTS;

AMINATION;

AZIDE; BENZILIC ACID; COBALT; COPPER COMPLEX; CUMENE; CYCLOHEXYLAMINE DERIVATIVE; FLUORENE DERIVATIVE; HYDROCARBON; ISOTOPE; PORPHYRIN; TOLUENE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; KINETICS; MOLECULAR MECHANICS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037415080     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390018     Document Type: Article

References (120)

1. a) M. Johannsen, K. A. Jorgensen, Chem. Rev. 1998, 98, 1689-1708 and references therein;
2. Modern Amination Methods (Ed.: A. Ricci), Wiley-VCH, Weinheim, 2000.
3. a) R. Breslow, S. H. J. Gellman, J. Chem. Soc. Chem. Commun. 1982, 1400-1401;
4. b) E. W. Svastits, J. H. Dawson, R. Breslow, S. H. Gellman, J. Am. Chem. Soc. 1985, 107, 6427-6428;
5. c) J.-P. Mahy, G. Bedi, P. Battioni, D. Mansuy. Tetrahedron Lett. 1988, 1927-1930;
6. d) J.-P. Mahy, G. Bedi, P. Battioni, D. Mansuy, New J. Chem. 1989, 13, 651-657;
7. e) I. Nageli, C. Baud, G. Bernardinelli, Y. Jaquier, M. Moran, P. Muller, Helv. Chim. Acta, 1997, 80, 1087-1105;
8. f) Y. Kohmura, T. Katsuki, Tetrahedron Lett. 2001, 42, 3339-3342;
9. g) J. Yang, R. Weinberg, R. Breslow, Chem. Commun. 2000, 531-532.
10. a) X.-G. Zhou, X.-Q. Yu, J.-S. Huang, C.-M. Che, Chem. Commun, 1999, 2377-2378;
11. b) J.-L. Liang, J.-S. Huang, X.-Q. Yu, N. Zhu, C.-M. Che, Chem. Eur. J. 2002, 8, 1563-1572.
12. a) S.-M. Au, J.-S. Huang, W.-Y. Yu, W.-H. Fung, C.-M. Che, J. Am. Chem. Soc. 1999, 121, 9120-9132;
13. b) X.-Q. Yu, J.-S. Huang, X.-G. Zhou, C.-M. Che, Org. Lett. 2000, 2, 2233-2236;
14. c) S.-M. Au, J.-S. Huang, W.-Y. Yu, C.-M. Che, W.-Y. Yu, J. Org. Chem. 2000, 65, 7858-7864;
15. d) C.-M. Che, W.-Y. Yu, Pure Appl. Chem. 1999, 71, 281-288;
16. e) S.-M. Au, S.-B. Zhang, W.-H. Fung. W.-Y. Yu, C.-M. Che, K.-K. Cheung, Chem. Commun. 1998, 2677-2678;
17. f) J.-L. Liang, W.-Y. Yu, C.-M. Che. Chem. Commun. 2002, 124-125.
18. a) S. Cenini, A. Penoni, S. Tollari, J. Mol. Catal. A 1997, 124, 109-113;
19. b) D. P. Albone, P. S. Aujla, P. C. Taylor, J. Org. Chem. 1998, 63, 9569-9571;
20. c) B. M. Chanda, R. Vyas, A. V. Bedekar, J. Org. Chem. 2001, 66, 30-34.
21. Y. Kohmura, K. Kawasaki, T. Katsuki, Synlett 1997, 1456-1458.
22. P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996. 96, 1123-1178.
23. a) S. Cenini, F. Ragaini, S. Tollari, D. Paone, J. Am. Chem. Soc. 1996, 118, 11, 964-11965;
24. b) F. Ragaini, S. Cenini, S. Tollari. G. Tummolillo, R. Beltrami, Organometallics 1999, 18, 928-942;
25. c) F. Ragaini, S. Cenini, E. Borsani, M. Dompé, E. Gallo, M. Moret Organometallics 2001, 20, 3390-3398.
26. S. Cenini, S. Tollari, A. Penoni, C. Cereda, J. Mol. Catal. A, 1999, 37, 135-146.
27. E. Gallo, F. Ragaini, C. Perrone, A. Penoni, S. Tollari, S. Cenini, unpublished results.
28. S. Cenini, E. Gallo, A. Penoni, F. Ragaini, S. Tollari Chem. Commun. 2000, 2265-2266.
29. a) M. C. Carreno, J. M. Cuerva, M. Ribagorda, A. M. Echavarren, Angew. Chem. 1999, 111, 1552-1555; Angew. Chem. Int. Ed. 1999, 38, 1449-1452;
30. a) M. C. Carreno, J. M. Cuerva, M. Ribagorda, A. M. Echavarren, Angew. Chem. 1999, 111, 1552-1555; Angew. Chem. Int. Ed. 1999, 38, 1449-1452;
31. b) M. Tokunaga, M. Eckert, Y. Wakatsuki, Angew. Chem. 1999, 111, 3416-3419; Angew. Chem. Int. Ed. 1999, 38, 3222-3225 and references therein.
32. b) M. Tokunaga, M. Eckert, Y. Wakatsuki, Angew. Chem. 1999, 111, 3416-3419; Angew. Chem. Int. Ed. 1999, 38, 3222-3225 and references therein.
33. J. P. Collman, J. E. Hutchison, M. S. Ennis, M. A. Lopez, R. Guilard, J. Am. Chem. Soc. 1992, 114, 8074-8080.
34. V. Briois, C. Cartier, M. Momenteau, P. Maillard, J. Zarembowitch, E. Dartyge, A. Fontaine, G. Tourillon, P. Thuery, M. Verdaguer Chim. Phys. Phys.-Chim. Biol. 1989, 86, 1623-1634.
35. [15b]
36. b) For a review see: R. S. Drago, B. B. Corden, Acc. Chem. Res. 1980, 13, 353-360.
37. C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165-195.
38. [18] (see also later) parameters.
39. Y.-D. Wu, C.-L. Wong, K. W. K. Chan, G.-Z. Ji, X.-K. Jiang, J. Org. Chem. 1996, 61, 746-750.
40. X.-K. Jiang, Acc. Chem. Res. 1997, 30, 283-289 and references therein.
41. a) J. F. Hartwig, Chem. Rev. 1998, 98, 2046-2067;
42. b) B. H. Yang, S. L. Buchwald, J. Organomet. Chem. 1999, 576, 125-146;
43. c) A. Klapars, J. C. Antilla, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727-7729;
44. d) S. Hayat, A. Rahman, M. I. Choudhary, K. M. Khan, W. Shumann, E. Bayer, Tetrahedron 2001, 57, 9951-9957;
45. e) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trautwein, Angew, Chem. 1998, 110, 3571-3573; Angew. Chem. Int. Ed. 1998, 37, 3389-339.
46. e) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trautwein, Angew, Chem. 1998, 110, 3571-3573; Angew. Chem. Int. Ed. 1998, 37, 3389-339.
47. a) N. C. Faibish, Y. S. Park, S. Lee, P. Beak, J. Am. Chem. Soc. 1997, 119, 11561-11570;
48. b) H. J. Koh, H. W. Lee, I. Lee, J. Chem. Soc. Perkin Trans. 2 1994, 125-129;
49. c) R. Chaabouni, A. Laurent, Bull. Soc. Chim. Fr. 1973, 2680-2685;
50. d) M. O. Abdel-Rahman, M. N. Aboul-Enein, G. H. Tamman, Egypt. J. Chem. 1975, 18, 581-586; Chem. Abstr. 1978, 89, 197017c.
51. d) M. O. Abdel-Rahman, M. N. Aboul-Enein, G. H. Tamman, Egypt. J. Chem. 1975, 18, 581-586; Chem. Abstr. 1978, 89, 197017c.
52. a) M. F. Budyka, M. M. Kantor, M. V. Alfimov Russ. Chem. Rev. 1992, 61, 25-39;
53. b) E. F. V. Scriven, K. Turnbull, Chem. Rev. 1988, 88, 297-368.
54. C. Ohta, T. Katsuki, Tetrahedron Lett. 2001, 42, 3885-3888.
55. T.-S. Lai, H.-L. Kwong, C.-M. Che, S,-M. Peng, Chem. Commun. 1997, 2373-2374.
56. M. M. Diaz-Requejo, P. J, Pérez, M. Brookhart, J. L. Templeton. Organometallics 1997, 16, 4399-4402.
57. F. H. Westheimer, Chem. Rev. 1961, 61, 265-273.
58. L. Melander, W. H. Saunders, Jr., Reaction Rates of Isotopic Molecules, Wiley-Interscience, New York, 1980.
59. M. Amin, R. C. Price, W. H. Saunders, Jr., J. Am. Chem. Soc. 1990, 112, 4467-4471.
60. [29c]
61. b) C.-M. Che, V. W.-W. Yam, Adv. Inorg. Chem. 1992, 39, 233-325 and references therein;
62. c) K. Yoshizawa, Coord. Chem. Rev. 2002, 226, 251-259 and references therein.
63. a) M. G. Fickes, W. M. Davis, C. C. Cummins, J. Am. Chem. Soc. 1995, 117, 6384-6385;
64. b) G. Proulx, R. G. Bergman, J. Am. Chem. Soc. 1995, 117, 6382-6383;
65. c) T. A. Hanna, A. M. Baranger, R. G. Bergman, Angew. Chem. 1996, 108, 693-696; Angew. Chem. Int. Ed. Engl. 1996, 35, 653-655;
66. c) T. A. Hanna, A. M. Baranger, R. G. Bergman, Angew. Chem. 1996, 108, 693-696; Angew. Chem. Int. Ed. Engl. 1996, 35, 653-655;
67. d) G. Proulx, R. G. Bergman, Organometallics 1996, 15, 684-692;
68. e) M. Barz, E. Herdtweck, W. R. Thiel, Angew. Chem. 1998, 110, 2380-2383; Angew. Chem. Int. Ed. 1998, 37, 2262-2265;
69. e) M. Barz, E. Herdtweck, W. R. Thiel, Angew. Chem. 1998, 110, 2380-2383; Angew. Chem. Int. Ed. 1998, 37, 2262-2265;
70. f) G. Guillemot, E. Solari, C. Floriani, C. Rizzoli, Organometallics 2001, 20, 607-615;
71. g) H. V. R. Dias, S. A. Polach, S.-K. Goh, E. F. Archibong, D. S. Marynick, Inorg. Chem. 2000, 39, 3894-3901;
72. h) I. Foch, L. Párkányi, G. Besenyei, L. I. Simándi, A. Kálmán, J. Chem. Soc. Dalton Trans. 1999, 293-299;
73. i) G. Besenyei, L. Párkányi, I. Foch, L. I. Simándi, Angew. Chem. 2000, 112, 986-988; Angew. Chem. Int. Ed. 2000, 39, 956-958.
74. i) G. Besenyei, L. Párkányi, I. Foch, L. I. Simándi, Angew. Chem. 2000, 112, 986-988; Angew. Chem. Int. Ed. 2000, 39, 956-958.
75. a) E. S. Lewis, H. L. Funderburk, J. Am. Chem. Soc. 1967, 89, 2322-2327;
76. b) B. T. Farrer, H. H. Thorp, Inorg. Chem. 1999, 38, 2497-2502.
77. R. D. Webster, G. A. Hearth, A. M, Bond, J. Chem. Soc. Dalton Trans. 2001, 3189-3195.
78. M. Tanno, S. Sueyoshi, S. Kamiya, Chem. Pharm. Bull. 1982, 30, 3125-3132.
79. R. A. W. Johnstone, M. L. P. G. Nunes, M. M. Pereira, A. M. d'A. Rocha Gonsalves, A. Serra, Heterocycles 1996, 43, 1423-1437.
80. a) A. Shirazi, H. M. Goff, Inorg. Chem. 1982, 21, 3420-3425;
81. b) A. D. Adler, F. R. Longo, V. Varadi, Inorg. Synth. 1976, 16, 213-220.
82. A. R. Katritzky, K. S. Laurenzo, J. Org. Chem. 1988, 53, 3978-3982.
83. S. Chandrasekhar, M. Venkat Reddy, L. Chandraiah, Synth. Commun. 1999, 29, 3981-3987.
84. T. Suwa, E. Sugiyama, I. Shibata, A. Baba, Synthesis 2000, 789-800.
85. R. Grigg, T. R. B. Mitchell, N. Tongpenyai, Synthesis 1981, 442-444.
86. K. Kanie, K. Mizuno, M. Kuroboshi, T. Hiyama. Bull. Chem. Soc. Jpn. 1998, 71, 1973-1991.
87. B. Carboni, M. Vaultier, T. Courgeon, R. Carriè, Bull. Soc. Chim. Fr. 1989, 844-849.
88. M. Tanaka, T. Kobayashi, Synthesis 1985, 967-969.
89. R. M. Lopez, G. C. Fu, Tetrahedron 1997, 53, 16349-16354.
90. L. Forlani, M. Sintoni, P. E. Todesco, Gazz. Chim. Ital. 1986, 116. 229-232.
91. S. Bennour, J. Toullec, Can. J. Chem. 1999, 77, 760-773.
92. J. R. Hwu, W. N. Tseng, H. V. Patel, F. F. Wong, D.-N. Horng, B. R. Liaw, L. C. Lin, J. Org. Chem. 1999, 64, 2211-2218.
93. A. Echevarria, J. Miller, M. G. Nascimento, Magn. Reson. Chem. 1985, 23, 809-813.
94. J. Dale, L. Vikersveen, Acta Chem. Scand. Set. B 1988, 42, 354-361.
95. Y.-Z. Li, J. P. Kirby, M. W. George, M. Polyakoff, G. B. Schuster, J. Am. Chem. Soc. 1988, 110, 8092-8098.
96. X.-Y. Wang, Y.-L. Wang, Z.-Y. Zhang, C.-L. Wang, J.-P. Li, L. Shi, Z.-F. Duan, Synth. Commun. 1999, 29, 481-485.
97. R. H. Lowack, R. Weiss, J. Am. Chem. Soc. 1990, 112, 333-338.
98. H. J. Koh, H. W. Lee, I. Lee, J Chem. Soc. Perkin Trans. 2, 1994, 125-129
99. a) Y. S. Andreichikov, Y. V. Ionov, Zh. Org. Khim. 1982, 18, 2430-2435; Russ. J. Org. Chem. 1982, 18, 2154-2158 (English translation);
100. a) Y. S. Andreichikov, Y. V. Ionov, Zh. Org. Khim. 1982, 18, 2430-2435; Russ. J. Org. Chem. 1982, 18, 2154-2158 (English translation);
101. b) B. I. Buzykin, G. D. Lezhnina, Y. P. Kitaev, Zh. Org. Khim. 1975, 11, 848-853; Russ. J. Org. Chem. 1975, 837-841 (English translation).
102. b) B. I. Buzykin, G. D. Lezhnina, Y. P. Kitaev, Zh. Org. Khim. 1975, 11, 848-853; Russ. J. Org. Chem. 1975, 837-841 (English translation).
103. a) J. W. Bae, S. H. Lee, Y. J. Cho, C. H. Yoon, J. Chem. Soc. Perkin Trans. 1 2000, 145-146;
104. b) A. Pelter, R. M. Rosser, S. Mills, J. Chem. Soc. Perkin Trans. 1 1984, 717-720.
105. a) J. P. Wolfe. H. Tomori, J. E. Sadighi, J. Yin, S. L. Buchwald, J. Org. Chem. 2000. 65, 1158-1174;
106. b) G. Reddelien, Chem. Ber. 1914, 47, 1355-1364;
107. c) W. A. Henderson, A. Zweig, Tetrahedron 1971, 27, 5307-5313;
108. d) H. Abu-Eittah, Bull. Chem. Soc. Jpn. 1974, 47, 2576-2579.
109. S. Chang, H. J. Koh, B.-S. Lee, I. Lee, J. Org. Chem. 1995, 60, 7760-7768.
110. H. K. Hall, Jr., A. B. Padias, P. A. Williams, J.-M. Gosau, H. W. Boone, D.-K. Park, Macromolecules 1995, 28, 1-8.
111. E. Alonso, D. J. Ramon, M. Yus, Tetrahedron 1997, 53, 14355-14368.
112. F. E, Baz, M. Rivère-Baudet, M. Ahra, J. Organomet. Chem. 1997, 548, 123-129.
113. J. Zemlicka, J. P. Horwitz, J. Org. Chem. 1971, 36, 2809-2812.
114. J. S. Sandhu, D. Mago, Tetrahedron Lett. 1975, 16, 1091-1092.
115. A. Bolognese, M. V. Diurno, O. Mazzoni, F. Giordano, Tetrahedron 1991, 47, 7417-7428.
116. I. I. Juchnovski. V. Ognyanova, Spectrosc. Lett. 1993, 26, 447-452.
117. E. Liepins, V. A. Pestunovich. A. V. Eremeev, D. A. Tikhomirov, N. P. Gaidarova. Khim. Geterotsikl. Soedin. 1977, 906-909; Chem. Abstr 1977, 87, 183795b.
118. E. Liepins, V. A. Pestunovich. A. V. Eremeev, D. A. Tikhomirov, N. P. Gaidarova. Khim. Geterotsikl. Soedin. 1977, 906-909; Chem. Abstr 1977, 87, 183795b.
119. O. H. Wheeler. P. H. Gore,J. Org. Chem. 1961, 26, 3298-3301;
120. J. Bernstein, I. Izak. J. Cryst. Mol. Struct, 1975, 5, 257-266.