Structural characterization and intramolecular aliphatic C-H oxidation ability of MIII(μ-O)2MIII complexes of Ni and Co with the hydrotris-(3,5-dialkyl-4-X-pyrazolyl)borate ligands TpMe2,X (X = Me, H, Br) and TpiPr2

Chemistry - A European Journal

Volumn 7, Issue 23, 2001, Pages 5012-5028

  Hikichi, Shiro ^a,b   Yoshizawa, Michito ^a   Sasakura, Yasuyuki ^a   Komatsuzaki, Hidehito ^a   Moro oka, Yoshihiko ^a   Akita, Munetaka ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

Cobalt; N ligands; Nickel; O ligands; Oxidation

Indexed keywords

CHEMICAL BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PARAMAGNETISM; PROTEINS; STRUCTURAL ANALYSIS; THERMODYNAMIC STABILITY;

LIGANDS;

NICKEL COMPOUNDS;

ALIPHATIC COMPOUND; BORIC ACID; COBALT COMPLEX; LIGAND; METAL COMPLEX; NICKEL COMPLEX; OXYGEN; PYRAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; INFRARED SPECTROSCOPY; KINETICS; MAGNETISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

COBALT; CRYSTALLOGRAPHY, X-RAY; LIGANDS; METALLOPROTEINS; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; OXYGEN; SPECTRUM ANALYSIS;

EID: 0035804139     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (127)

1. a) Metal-Catalyzed Oxidations of Organic Compounds (Eds.: R. A. Sheldon, J. K. Kochi), Academic Press, New York, 1981;
2. b) "Bioinorganic Enzymology": Chem. Rev. 1996, 96, 2237-3042 (special thematic issue);
3. c) "Metal-Oxo and Metal-Peroxo Species in Catalytic Oxidations": Struct. Bonding 2000, 97, 1-303.
4. a) L. Que, Jr., Y. Dong, Acc. Chem. Res. 1996, 29, 190-196;
5. b) L. Que, Jr., J. Chem. Soc. Dalton Trans. 1997, 3933-3940.
6. a) W. B. Tolman, Acc. Chem. Res. 1997, 30, 227-237;
7. b) P. Holland, W. B. Tolman, Coord. Chem. Rev. 1999, 190-192, 855-869.
8. a) L. Shu, J. C. Nesheim, K. Kauffmann, E. Münck, J. D. Lipscomb, L. Que, Jr., Science 1997, 275, 515-518;
9. b) A. M. Valentine, S. S. Stahl, S. J. Lippard, J. Am. Chem. Soc. 1999, 121, 3876-3887;
10. c) A. M. Valentine, S. J. Lippard, J. Chem. Soc. Dalton Trans. 1997, 3925-3931.
11. S. J. Elliott, M. Zhu, L. Tso, H.-H. T. Nguyen, J. H.-K. Yip, S. I. Chan, J. Am. Chem. Soc. 1997, 119, 9949-9955.
12. E. Mulliez, M. Fontecave, Chem. Ber./Recl. 1997, 130, 317-321.
13. a) E. I. Solomon, T. C. Brunold, M. I. Davis, J. N. Kemsley, S.-K. Lee, N. Lehnert, F. Neese, A. J. Skulan, Y.-S. Yang, J. Zhou, Chem. Rev. 2000, 100, 235-349;
14. b) B. J. Wallar, J. D. Lipscomb, Chem. Rev. 1996, 96, 2625-2657.
15. a) M. H. Gubelmann, A. F. Williams, Struct. Bonding 1983, 55, 1-65;
16. b) "Metal-Dioxygen Complexes": Chem. Rev. 1994, 94, 567-856 (special thematic issue).
17. N. Kitajima, W. B. Tolman, Prog. Inorg. Chem. 1995, 43, 419-531.
18. N. Kitajima, Y. Moro-oka, Chem. Rev. 1994, 94, 737-757.
19. a) N. Kitajima, K. Fujisawa, Y. Moro-oka, J. Am. Chem. Soc. 1989, 111, 8975-8976;
20. b) N. Kitajima, K. Fujisawa, C. Fujimoto, Y. Morooka, S. Hashimoto, T. Kitagawa, K. Toriumi, K. Tatsumi, A. Nakamura, J. Am. Chem. Soc. 1992, 114, 1277-1291.
21. 2-peroxodi-copper(ii) complexes: a) M. Kodera, K. Katayama, Y. Tachi, K. Kano, S. Hirota, S. Fujinami, M. Suzuki, J. Am. Chem. Soc. 1999, 121, 11006-11007;
22. b) B. M. T. Lam, J. A. Halfen, V. G. Young, Jr., J. R. Hagadorn, P. L. Holland, A. Lledós, L. Cucurull-Sánchez, J. J. Novoa, S. Alvarez, W. B. Tolman, Inorg. Chem. 2000, 39, 4059-4072.
23. M. J. Baldwin, D. E. Root, J. E. Pate, K. Fujisawa, N. Kitajima, E. I. Solomon, J. Am. Chem. Soc. 1992, 114, 10421-10431.
24. N. Kitajima, T. Koda, Y. Iwata, Y. Moro-oka, J. Am. Chem. Soc. 1990, 112, 8833-8839.
25. a) J. A. Halfen, S. Mahapatra, E. C. Wilkinson, S. Kaderli, V. G. Young, Jr., L. Que, Jr., A. D. Zuberbühler, W. B. Tolman, Science 1996, 271, 1397-1400;
26. b) S. Mahapatra, J. A. Halfen, E. C. Wilkinson, G. Pan, X. Wang, V. G. Young, Jr., C. J. Cramer, L. Que, Jr., W. B. Tolman, J. Am. Chem. Soc. 1996, 118, 11555-11574;
27. c) S. Mahapatra, J. A. Halfen, W. B. Tolman, J. Am. Chem. Soc. 1996, 118, 11575-11586.
28. 2 complexes: a) S. Mahapatra, V. G. Young, Jr., S. Kaderli, A. D. Zuberbühler, W. B. Tolman, Angew. Chem. 1997, 109, 125-127;
29. Angew. Chem. Int. Ed. Engl. 1997, 36, 130-133;
30. b) V. Mahadevan, Z. Hou, A. P. Cole, D. E. Root, T. K. Lal, E. I. Solomon, T. D. P. Stack, J. Am. Chem. Soc. 1997, 119, 11996-11997;
31. c) H. Hayashi, S. Fujinami, S. Nagatomo, S. Ogo, M. Suzuki, A. Uehara, Y. Watanabe, T. Kitagawa, J. Am. Chem. Soc. 2000, 122, 2124-2125;
32. d) B. F. Straub, F. Rominger, P. Hofmann, Chem. Commun. 2000, 1611-1612.
33. 2: a) M. Kosugi, S. Hikichi, M. Akita, Y. Moro-oka, J. Chem. Soc. Dalton Trans. 1999, 1369-1371;
34. Mn-OO(R): b) H. Komatsuzaki, Y. Nagasu, K. Suzuki, T. Shibasaki, M. Satoh, F. Ebina, S. Hikichi, M. Akita, Y. Moro-oka, J. Chem. Soc. Dalton Trans. 1998, 511-512;
35. c) H. Komatsuzaki, M. Satoh, N. Sakamoto, S. Hikichi, M. Akita, Y. Moro-oka, Inorg. Chem. 1998, 37, 6554-996;
36. Fe-catecholate oxygenation: d) T. Ogihara, S. Hikichi, M. Akita, Y. Moro-oka, Inorg. Chem. 1998, 37, 2614-2615;
37. Fe-OOR: e) T. Ogihara, S. Hikichi, M. Akita, T. Uchida, T. Kitagawa, Y. Moro-oka, Inorg. Chim. Acta 2000, 297, 162-170;
38. oxidative C-C bond cleavage by Ru complex: f) Y. Takahashi, S. Hikichi, M. Akita, Y. Moro-oka, Chem. Commun. 1999, 1491-1492;
39. 2: g) Y. Takahashi, M. Hashimoto, S. Hikichi, M. Akita, Y. Moro-oka, Angew. Chem. 1999, 111, 3259-3262;
40. Angew. Chem. Int. Ed. 1999, 38, 3074-3077;
41. Pd-OO(R): h) M. Akita, T. Miyaji, S. Hikichi, and Y. Moro-oka, Chem. Commun. 1998, 1005-1006;
42. i) M. Akita, T. Miyaji, S. Hikichi, Y. Moro-oka, Chem. Lett. 1999, 813-814;
43. review: j) M. Akita, S. Hikichi, Y. Moro-oka, J. Synth. Org. Chem. 1999, 57, 619-628.
44. S. Hikichi, H. Komatsuzaki, M. Akita, Y. Moro-oka, J. Am. Chem. Soc. 1998, 120, 4699-4710.
45. a) S. Trofimenko, Scorpionates - The Coordination Chemistry of Polypyrazolylborate Ligands, Imperial College Press, London, 1999;
46. b) S. Torofimenko, Chem. Rev. 1993, 93, 943-980.
47. Similar concept was applied to the copper-dioxygen complex chemistry reported by Stack and co-workers (ref. [16b]).
48. Mn: a) N. Kitajima, U. P. Singh, H. Amagai, M. Osawa, Y. Moro-oka, J. Am. Chem. Soc. 1991, 113, 7757-7758, and see also ref. [10c];
49. Fe: b) N. Kitajima, N. Tamura, M. Tanaka, Y. Moro-oka, Inorg. Chem. 1992, 31, 3342-3343, and see also ref. [10e];
50. Co, Ni, Zn: c) N. Kitajima, S. Hikichi, M. Tanaka, Y. Moro-oka, J. Am. Chem. Soc. 1993, 115, 5496-5508, and see also ref. [15];
51. Cu: d) K. Fujisawa, T. Kobayashi, K. Fujita, N. Kitajima, Y. Moro-oka, Y. Miyashita, Y. Yamada, K. Okamoto, Bull. Chem. Soc. Jpn. 2000, 73, 1797-1804, and see also ref. [11];
52. Pd: e) M. Akita, T. Miyaji, N. Muroga, C. Mock-Knoblauch, W. Adam, S. Hikichi, Y. Moro-oka, Inorg. Chem. 2000, 39, 2096-2102;
53. review: f) G. Parkin, Adv. Inorg. Chem. 1995, 42, 291-393.
54. S. Hikichi, Y. Sasakura, M. Yoshizawa, Y. Ohzu, Y. Moro-oka, M. Akita, unpublished results.
55. M. Akita, K. Ohta, Y. Takahashi, S. Hikichi, Y. Moro-oka, Organometallics 1997, 16, 4121-4128.
56. S. Hikichi, Y. Yoshizawa, Y. Sasakura, M. Akita, Y. Moro-oka, J. Am. Chem. Soc. 1998, 120, 10567-10568.
57. U. Bemm, R. Norrestam, M. Nygren, G. Westin, Inorg. Chem. 1993, 32, 1597-1600.
58. The structure of the six-coordinated bis(μ-oxo)dinickel(III) complex has been reported: K. Shiren, S. Ogo, S. Fujinami, H. Hayashi, M. Suzuki, A. Uehara, Y. Watanabe, Y. Moro-oka, J. Am. Chem. Soc. 2000, 122, 254-262.
59. 2(μ-O)], was reported: B. Bag, N. Mondal, G. Rosair, S. Mitra, Chem. Commun. 2000, 1729-1730.
60. 8] has been reported, but the formal valence of the Ni centers is not clear: R. Gottschall, R. Schöllhorn, M. Muhler, N. Jansen, D. Walcher, P. Gütlich, Inorg. Chem. 1998, 37, 1513-1518.
61. M. J. Henson, P. Mukherjee, D. E. Root, T. D. P. Stack, E. I. Solomon, J. Am. Chem. Soc. 1999, 121, 10332-10345.
62. S. Itoh, H. Bandoh, S. Nagatomo, T. Kitagawa, S. Fukuzumi, J. Am. Chem. Soc. 1999, 121, 8945-8946.
63. a) K. Dimitrou, K. Folting, W. E. Streib, G. Christou, J. Am. Chem. Soc. 1993, 115, 6432-6433;
64. b) K. Dimitrou, K. Folting, W. E. Streib, G. Christou, J. Chem. Soc. Chem. Commun. 1994, 1385-1386;
65. c) K. Dimitrou, J.-S. Sun, K. Folting, G. Christou, Inorg. Chem. 1995, 34, 4160-4166;
66. d) K. Dimitrou, A. D. Brown, K. Folting, G. Christou, Inorg. Chem. 1999, 38, 1834-1841;
67. e) J. K. Beattie, T. W. Hambley, J. A. Klepetko, A. F. Masters, P. Turner, Polyhedron, 1998, 17, 1343-1354;
68. f) T. Ama, K. Okamoto, T. Yonemura, H. Kawaguchi, Y. Ogasawara, T. Yasui, Chem. Lett. 1997, 29-30;
69. g) T. Ama, K. Okamoto, T. Yonemura, H. Kawaguchi, A. Takeuchi, T. Yasui, Chem. Lett. 1997, 1189-1190;
70. h) T. Ama, M. M. Rashid, T. Yonemura, H. Kawaguchi, T. Yasui, Coord. Chem. Rev. 2000, 198, 101-116.
71. a) P. B. Hitchcock, G. M. McLaughlin, J. Chem. Soc. Dalton Trans. 1976, 1927-1930;
72. b) N. A. Bailey, E. D. McKenzie, J. M. Worthington, J. Chem. Soc. Dalton Trans. 1977, 763-767;
73. c) L. H. Doerrer, M. T. Bautista, S. J. Lippard, Inorg. Chem. 1997, 36, 3578-3579;
74. d) M. D. Fryzuk, D. B. Leznoff, R. C. Thompson, S. J. Rettig, J. Am. Chem. Soc. 1998, 120, 10126-10135;
75. e) B. S. Hammes, V. G. Young, Jr., A. S. Borovik, Angew. Chem. 1999, 111, 744-746;
76. Angew. Chem. Int. Ed. 1999, 38, 666-669.
77. a) O. J. Curnow, B. K. Nicholson, J. Organomet. Chem. 1984, 267, 257-263;
78. b) A. Hayashi, K. Nakajima, M. Nonoyama, Polyhedron 1997, 16, 4087-4095.
79. S. Hikichi, H. Komatsuzaki, N. Kitajima, M. Akita, M. Mukai, T. Kitagawa, Y. Moro-oka, Inorg. Chem. 1997, 36, 266-267.
80. a) O. M. Reinaud, K. H. Theopold, J. Am. Chem. Soc. 1994, 116, 6979-6980;
81. b) O. M. Reinaud, G. P. A. Yap, A. L. Rheingold, K. H. Theopold, Angew. Chem. 1995, 107, 2171-2173;
82. Angew. Chem. Int. Ed. Engl. 1995, 34, 2051-2052.
83. K. H. Theopold, O. M. Reinaud, D. Doren, R. Konecny, in 3rd World Congress on Oxidation Catalysis (Eds.: R. K. Grasselli, S. T. Oyama, A. M. Gaffney, J. E. Lyons), Elsevier, Amsterdam, 1997, pp. 1081-1088.
84. J. Cahoy, P. L. Holland, W. B. Tolman, Inorg. Chem. 1999, 38, 2161-2168.
85. a) H. V. Obias, Y. Lin, N. N. Murthy, E. Pidcock, E. I. Solomon, M. Ralle, N. J. Blackburn, Y.-M. Neuhold, A. D. Zuberbuhler, K. D. Karlin, J. Am. Chem. Soc. 1998, 120, 12960-12961;
86. b) E. Pidcock, S. DeBeer, H. V. Obias, B. Hedman, K. O. Hodgson, K. D. Karlin, E. I. Solomon, J. Am. Chem. Soc. 1999, 121, 1870-1878.
87. N. Kitajima, T. Koda, S. Hashimoto, T. Kitagawa, Y. Moro-oka, J. Am. Chem. Soc. 1991, 113, 5664-5671.
88. a) Y. Zang, Y. Dong, L. Que, Jr., K. Kauffman, E. Münck, J. Am. Chem. Soc. 1995, 117, 1169-1170;
89. b) H. Zheng, Y. Zang, Y. Dong, V. G. Young, Jr., L. Que, Jr., J. Am. Chem. Soc. 1999, 121, 2226-2235;
90. c) H.-F. Hsu, Y. Dong, L. Shu, V. G. Young, Jr., L. Que, Jr., J. Am. Chem. Soc. 1999, 121, 5230-5237.
91. V. L. MacMurdo, H. Zheng, L. Que, Jr., Inorg. Chem. 2000, 39, 2254-2255.
92. S. Hikichi, Y. Yoshizawa, M. Yoshizawa, Y. Moro-oka, M. Akita, unpublished results.
93. a) P. L. Holland, K. R. Rodgers, W. B. Tolman, Angew. Chem. 1999, 111, 1210-1213;
94. Angew. Chem. Int. Ed. 1999, 38, 1139-1142;
95. b) V. Mahadevan, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, J. Am. Chem. Soc. 1999, 121, 5583-5584;
96. c) S. Itoh, M. Taki, H. Nakao, P. L. Holland, W. B. Tolman, L. Que, Jr., S. Fukuzumi, Angew. Chem. 2000, 112, 409-411;
97. Angew. Chem. Int. Ed. 2000, 59, 398-400;
98. d) S. Itoh, H. Nakao, L. M. Berreau, T. Kondo, M. Komatsu, S. Fukuzumi, J. Am. Chem. Soc. 1998, 120, 2890-2899;
99. e) I. Blain, P. Bruno, M. Giorgi, E. Lojou, D. Lexa, M. Réglier, Eur. J. Inorg. Chem. 1998, 1297-1304;
100. f) I. Blain, M. Giorgi, I. De Riggi, M. Réglier, Eur. J. Inorg. Chem. 2000, 393-398;
101. g) W. E. Allen, T. N. Sorrell, Inorg. Chem. 1997, 36, 1732-1734.
102. a) C. Kim, Y. Dong, L. Que, Jr., J. Am. Chem. Soc. 1997, 119, 3635-3636;
103. b) Y. Dong, Y. Zang, L. Shu, E. C. Wilkinson, L. Que, Jr., K. Kauffmann, E. Münck, J. Am. Chem. Soc. 1997, 119, 12683-12684;
104. c) D. Lee, S. J. Lippard, J. Am. Chem. Soc. 1998, 120, 12153-12154;
105. d) D. Lee, J. Du Bois, D. Petasis, M. P. Hendrich, C. Krebs, B. H. Hunyh, S. J. Lippard, J. Am. Chem. Soc. 1999, 121, 9893-9894;
106. e) J. R. Hagadorn, L. Que, Jr., W. B. Tolman, J. Am. Chem. Soc. 1998, 120, 13531-13532;
107. f) D. Lee, S. J. Lippard, J. Am. Chem. Soc. 2001, 123, 4611-4612.
108. a) K. Wang, J. M. Mayer, J. Am. Chem. Soc. 1997, 119, 1470-1471;
109. b) M. A. Lockwood, K. Wang, J. M. Mayer, J. Am. Chem. Soc. 1999, 121, 11894-11895.
110. S. Mahapatra, J. A. Halfen, E. C. Wilkinson, L. Que, Jr., W. B. Tolman, J. Am. Chem. Soc. 1994, 116, 9785-9786.
111. 1H NMR spectra of the same samples clearly indicated that the starting bis(μ-oxo) complexes 2a were consumed completely.
112. S. Hikichi, M. Yoshizawa, Y. Sasakura, H. Komatsuzaki, M. Akita, Y. Moro-oka, Chem. Lett. 1999, 979-980.
113. C. Bianchini, R. W. Zoellner, Adv. Inorg. Chem. 1996, 44, 263-339.
114. S. Hikichi, M. Akita, Y. Morooka, Coord. Chem. Rev. 2000, 198, 61-87, and references therein.
115. A. Bérces, Inorg. Chem. 1997, 36, 4831-4837.
116. Y. Hayashi, M. Obata, M. Suzuki, A. Uehara, Chem. Lett. 1997, 1255-1256.
117. a) N. Shirasawa, T. T. Nguyet, S. Hikichi, Y. Moro-oka, M. Akita, Organometallics 2001, 20, 3582-3598;
118. b) J. D. Jewson, L. M. Liable-Sands, G. P. A. Yap, A. L. Rheingold, K. H. Theopold, Organometallics 1999, 18, 300-305.
119. H3): D. M. Eichhorn, W. H. Armstrong, Inorg. Chem. 1990, 29, 3607-3612.
120. A. Ohsawa, T. Kaihoh, T. Itoh, M. Okada, C. Kawabata, K. Yamaguchi, H. Igeta, Chem. Pharm. Bull. 1988, 36, 3838-3848.
121. a) A. Albinati, M. Bovens, H. Ruegger, L. M. Venanzi, Inorg. Chem. 1997, 36, 5991-5999;
122. b) A. Wlodarczyk, R. M. Richardson, M. D. Ward, J. A. McCleverty, M. H. B. Hursthouse, S. J. Coles, Polyhedron 1996, 15, 27-35.
123. teXsan, ver. 1.11, Rigaku Corporation, Tokyo (Japan), 2000.
124. International Tables for X-Ray Crystallography, Vol. 4, Kynoch Press, Birmingham, 1975.
125. G. M. Sheldrick, SHELXS-86, University of Göttingen, 1986.
126. P. T. Beurskens, G, Admiraal, G. Beurskens, W. P. Bosman, S. Garcia-Granda, R. O. Gould, J. M. M. Smith, C. Smykalla, DIRDIF 92, University of nijmegen, 1992.
127. G. M. Sheldrick, SHELXL-97, University of Göttingen, 1997.