Bis axial ligation of simple imine and methyleneamido groups by ruthenium porphyrins

Chemistry - A European Journal

Volumn 6, Issue 16, 2000, Pages 2971-2981

  Huang, Jie Sheng ^a   Leung, Sarana Ka Yan ^a   Cheung, Kung Kai ^a   Che, Chi Ming ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Imines; Macrocyclic ligands; Methyleneamides; N ligands; Ruthenium; Structure elucidation

Indexed keywords

AMIDE; IMINE; PORPHYRIN DERIVATIVE; RUTHENIUM DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR INTERACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034683092     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20000818)6:16<2971::AID-CHEM2971>3.0.CO;2-#     Document Type: Article

References (131)

1. a) S. E. Diamond, G. M. Tom, H. Taube, J. Am. Chem. Soc. 1975, 97, 2661;
2. b) T. B. Gunnoe, P. S. White, J. L. Templeton, J. Am. Chem. Soc. 1996, 118, 6916.
3. a) K. G. Rasmussen, R. G. Hazell, K. A. Jørgensen, Chem. Commun. 1997, 1103;
4. b) K. G. Rasmussen, K. Juhl, R. G. Hazell, K. A. Jørgensen, J. Chem. Soc. Perkin Trans 2 1998, 1347.
5. G. K. Cantrell, T. Y. Meyer, J. Am. Chem. Soc. 1998, 120, 8035.
6. G. Mann, J. F. Hartwig, M. S. Driver, C. Fernández-Rivas, J. Am. Chem. Soc. 1998, 120, 827.
7. a) B. Meunier, Chem. Rev. 1992, 92, 1411;
8. b) J. P. Collman, X. M. Zhang, V. J. Lee, E. S. Uffelman, J. I. Brauman, Science 1993, 261, 1404;
9. c) D. Mansuy, Coord, Chem. Rev. 1993, 125, 129;
10. d) J. W. Buchler, C. Dreher, F. M. Runzel, Struct. Bonding (Berlin) 1995, 84, 1.
11. Selected examples: a) P. S. Traylor, D. Dolphin, T. G. Traylor, J. Chem. Soc. Chem. Commun. 1984, 279;
12. b) P. E. Ellis, Jr., J. E. Lyons, Coord. Chem. Rev. 1990, 105, 181;
13. c) H. Ohtake, T. Higuchi, M. Hirobe, J. Am. Chem. Soc. 1992, 114, 10660;
14. d) J. P. Collman, Z. Wang, A. Straumanis, M. Quelquejeu, J. Am. Chem. Soc. 1999, 121, 460.
15. M. Cetinkaya, A. W. Johnson, M. F. Lappert, G. M. McLaughlin, K. W. Muir, J. Chem. Soc. Dalton Trans. 1974, 1236.
16. a) C. Morice, P. Le Maux, G. Simonneaux, Tetrahedron Lett. 1996, 37, 6701;
17. b) C. Morice, P. Le Maux, C. Moinet, G. Simonneaux, Inorg. Chim. Acta 1998, 273, 142.
18. a) S.-M. Au, W.-H. Fung, M.-C. Cheng, C-M. Che, S.-M. Peng, Chem. Commun. 1997, 1655;
19. b) S.-M. Au, J.-S. Huang, W.-Y. Yu, W.-H. Fung, C-M. Che, J. Am. Chem. Soc. 1999, 121, 9120.
20. a) M. A. Andrews, H. D. Kaesz, J. Am. Chem. Soc. 1979, 101, 7255;
21. b) S. Itsuno, M. Sasaki, S. Kuroda, K. Ito, Tetrahedron Asymmetry 1995, 6, 1507.
22. a) F. A. Cotton, G. Wilkinson, Advanced Inorganic Chemistry, 5th ed., Wiley, New York, 1988, p. 371;
23. b) B. F. G. Johnson, B. L. Haymore, J. R. Dilworth in Comprehensive Coordination Chemistry, Vol. 2 (Eds.: G. Wilkinson, R. D. Gillard, J. A. McCleverty). Pergamon Press, Oxford, 1987, p. 99.
24. a) J. W. Buchler in Porphyrins and Metalloporphyrins (Ed.: K. M. Smith), Elsevier, Amsterdam, 1975, p. 157;
25. b) J. W. Buchler in The porphyrins, Vol. 1 (Ed.: D. Dolphin), Academic, New York, 1978, p. 389;
26. c) T. Mashiko, D. Dolphin in Comprehensive Coordination Chemistry, Vol. 2 (Eds.: G. Wilkinson, R. D. Gillard, J. A. McCleverly), Pergamon, Oxford, 1987, p. 813.
27. a) T. S. Srivastava, L. Hoffman, M. Tsutsui, J. Am. Chem. Soc. 1972, 94, 1385;
28. b) B. B. Wayland, E. W. Olson, J. Am. Chem. Soc. 1974, 96, 6037;
29. c) D. Lancon, K. M. Kadish, J. Am. Chem. Soc. 1983, 105, 5610;
30. d) J. W. Buchler, P. D. Smith, Chem. Ber. 1976, 109, 1465;
31. e) J. W. Buchler, W. Kokisch, P. D. Smith, Struct. Bonding (Berlin) 1978, 34, 79;
32. f) A. Antipas, J. W. Buchler, M. Gouterman, P. D. Smith, J. Am. Chem. Soc. 1980, 102, 198;
33. g) B. B. Wayland, J. V. Minkiewicz, J. Chem. Soc. Chem. Commun. 1976, 1015.
34. 2 =meso-tetrakis(3,4,5-trimethoxyphenyl)porphyrinato.
35. Comprehensive Coordination Chemistry (Eds.: G. Wilkinson, R. D. Gillard, J. A. McCleverty), Pergamon, Oxford, 1987.
36. Cr complexes: a) E. O. Fischer, L. Knauss, Chem. Ber. 1970, 103, 1262;
37. b) R. B. King, W. M. Douglas, Inorg. Chem. 1974, 13, 1339.
38. Mo complexes: B. S. McGilligan, T. C. Wright, G. Wilkinson, M. Motevalli, M. B. Hursthouse, J. Chem. Soc. Dalton Trans. 1988, 1737.
39. W complexes: a) See refs. [1b] and [16b];
40. b) S. G. Feng, J. E. Templeton, Organometullics 1992, 11, 1295;
41. c) W.-Y. Yeh, C.-S. Ting, S.-M. Peng, G.-H. Lee, Organometallics 1995, 14, 1417;
42. d) E. W. Francisco, P. S. White, J. E. Templeton, Organometallics 1996, 15, 5127.
43. Re complexes: a) J. Milke, C. Missling, K. Sunkel, W. Beck, J. Organomet. Chem. 1993, 445, 219;
44. b) D. A. Knight, M. A. Dewey, G. A. Stark, B. K. Bennett, A. M. Arif, J. A. Gladysz, Organometallics 1993, 12, 4523;
45. c) G. A. Stark, J. A. Gladysz, Inorg. Chem. 1996, 35, 5509;
46. d) G. A. Stark, J. A. Gladysz, Inorg. Chim. Acta 1998, 269, 167.
47. Fe complexes: M. F. Mayer, M. M. Hossain, J. Org. Chem. 1998, 63, 6839.
48. Ru complexes: a) C. P. Guengerich, K. Schug, J. Am. Chem. Soc. 1977, 99, 3298;
49. b) P. A. Adcock, F. R. Keene, J. Am. Chem. Soc. 1981, 103, 6494;
50. c) P. A. Adcock, F. R. Keene, R. S. Smythe, M. R. Snow, Inorg. Chem. 1984, 23, 2336;
51. d) J. W. Faller, Y. Ma, C. J. Smart, M. J. DiVerdi, J. Organomet. Chem. 1991, 420, 237;
52. e) K.-Y. Wong, C.-M. Che, C.-K. Li, W.-H. Chiu, Z. Y. Zhou, T. C. W. Mak, J. Chem. Soc. Chem. Commun. 1992, 754;
53. f) T. Rappert, A. Yamamoto, Chem. Lett. 1994, 2211;
54. g) C. Bohanna, M. A. Esteruelas, A. M. López, E. A. Oro, J. Organomet. Chem. 1996, 526, 73;
55. h) see ref. [19a].
56. Os complex: a) W. D. Harman, H. Taube, Inorg. Chem. 1988, 27, 3261;
57. b) M. J. Albeniz, M. E. Buil, M. A. Esteruelas, A. M. López, J. Orgnnomet. Chem. 1997, 546, 495.
58. Rh complex: A. G. Becalski, W. R. Cullen, M. D. Fryzuk, B. R. James, G.-J. Kang, S. J. Rettig, Inorg. Chem. 1991, 30, 5002.
59. Pt complexes: R. J. Cross, M. F. Davidson, M. Rocamora, J. Chem. Soc. Dalton Trans. 1988, 1147.
60. Cu complexes: W. Schneider, A. Bauer, H. Schmidbaur, Chem. Ber./ Recueil 1997, 130, 947.
61. Ag and Au complexes: W. Schneider, A. Bauer, H. Schmidbaur, J. Chem. Soc. Dalton Trans. 1997, 415.
62. For recent examples, see: a) G. Erker, W. Frömberg, C. Krüger, E. Raabe, J. Am. Chem. Soc. 1988, 110, 2400;
63. b) A. J. E. Pombeiro, D. E. Hughes, R. E. Richards, J. Chem. Soc. Chem. Commun. 1988, 1052;
64. c) A. J. E. Pombeiro, Inorg. Chim. Acta 1992, 200, 179;
65. d) C. Lefeber, P. Arndt, A. Tillack, W. Baumann, R. Kempe, V. V. Burlakov, U. Rosenthal, Organometallics 1995, 14, 3090;
66. e) P. A. Shapley, J. M. Shusta, J. E. Hunt, Organometallics 1996, 75, 1622;
67. f) N. C. MöschZanetti, R. R. Schreck, W. M. Davis, K. Wanninger, S. W. Seidel, M. B. O'Donoghue, J. Am. Chem. Soc. 1997, 119, 11037;
68. g) C. M. P. Ferreira, M. F. C. Guedes da Silva, V. Y. Kukushkin, J. J. R. Fraüsto da Silva, A. J. E. Pombeiro, J. Chem. Soc. Dalton Trans. 1998, 325;
69. h) J. E. Koch, P. A. Shapley, Organometallics 1999, 18, 814.
70. a) B. F. G. Johnson, J. A. McCleverty, Prog. Inorg. Chem. 1966, 7, 277;
71. b) J. H. Enemark, R. D. Feltham, Coord. Chem. Rev. 1974, 13, 339;
72. c) K. G. Caulton, Coord. Chem. Rev. 1975, 14, 317;
73. d) J. A. McCleverty, Chem. Rev. 1979, 79, 53;
74. c) K. K. Pandey, Coord. Chem. Rev. 1983, 51, 69;
75. f) W. L. Gladfelter, Adv. Organomet. Chem. 1985, 24, 41;
76. g) D. Michael, P. Mingos, D. J. Sherman, Adv. Inorg. Chem. 1989, 34, 293.
77. a) W. A. Nugent, B. L. Haymore, Coord. Chem. Rev. 1980, 31, 123;
78. b) W. A. Nugent, J. M. Mayer, Metal-Ligand Multiple Bonds, Wiley-Interscience, New York, 1988;
79. c) D. E. Wigley, Prog. Inorg. Chem. 1994, 42, 239.
80. a) D. C. Bradley, M. H. Chisholm, Acc. Chem. Res. 1976, 9, 273;
81. b) H. E. Bryndza, W. Tam, Chem. Rev. 1988, 88, 1163;
82. c) M. D. Fryzuk, C. D. Montgomery, Coord. Chem. Rev. 1989, 95, 1.
83. a) J. W. Buchler, S. Pfeifer, Z. Naturforsch. B: Inorg. Chem. Org. Chem. 1985, 40B, 1362;
84. b) R. L. Elliott, P. J. Nichols, B. O. West, Polyhedron 1987, 12, 2191;
85. c) J. A. Smieja, K. M. Omberg, G. L. Breneman, Inorg. Chem. 1994, 33, 614;
86. d) L. M. Berreau, V. G. Young, Jr., L. K. Woo, Inorg. Chem. 1995, 34, 527;
87. e) S. D. Gray, J. L. Thorman, L. M. Berreau, L. K. Woo, Inorg. Chem. 1997, 36, 278;
88. f) W. H. Leung, T. S. M. Hun, H.-W. Hou, K.-Y. Wong, J. Chem. Soc. Dalton Trans. 1997, 237;
89. g) J. L. Thorman, I. A. Guzei, V. G. Young, Jr., L. K. Woo, Inorg. Chem. 1999, 38, 3814.
90. a) J.-S. Huang, X.-R. Sun, S. K.-Y. Leung, K.-K. Cheung, C.-M. Che, Chem. Eur. J. 2000, 6, 334;
91. b) J.-S. Huang, C.-M. Che, Z.-Y. Li, C.-K. Poon, Inorg. Chem. 1992, 31, 1313;
92. c) J.-S. Huang, C.-M. Che, C.-K. Poon, J. Chem. Soc. Chem. Commun. 1992, 161;
93. d) C.-M. Che, J.-S. Huang, Z.-Y. Li, C.-K. Poon, Inorg. Chim. Acta 1991, 190, 161.
94. a) A. J. Bailey, B. R. James, Chem. Commun. 1996, 2343;
95. 2 =meso-tetrakis(2,4,6-trimethylphenyl)porphyrinato.
96. 14 (977.29, a product recrystallized from dichloromethane/n-hexane): calcd: C 72.51, H 6.91, N 8.59; found: C 72.32, H 6.78, N 8.30.
97. a) Both cytochrome P-450 and synthetic metalloporphyrins are known to catalyze N-dealkylation of tertiary amines. Metal-oxo species are proposed as the key intermediates in these processes. However, to our knowledge, there are no reports on the N-dealkylation by isolated oxo metalloporphyrins, see: J. R. Lindsay Smith, D. N. Mortimer, J. Chem. Soc. Perkin Trans 11 1986, 1743;
98. b) M. M. T. Khan, D. Chatterjee, S. Kumar, R. R. Merchant, K. N. Bhatt, J. Mol. Catalysis 1991, 67, 317.
99. a) N. Farrell, D. H. Dolphin, B. R. James, J. Am. Chem. Soc. 1978, 100, 324;
100. b) J. T. Groves, K.-H. Ahn, R. Quinn, J. Am. Chem. Soc. 1988, 110, 4217.
101. Synthesized by the standard method for the preparation of bis(pyridine)ruthenium(II) porphyrins, see: a) F. R. Hopf, T. P. O'Brien, W. R. Scheidt, D. G. Whitten, J. Am. Chem. Soc. 1975, 97, 277;
102. +.
103. The free N(Et)=CHMe ligand exhibits the ethylidene CH proton resonances at δ = 7.63 (C. Stevens, N. D. Kimpe, J. Org. Chem. 1993, 58, 132). Formation of 5a shifted such resonances upfield by 6.18 ppm, a value very similar to the upfield shift of 6.14 ppm observed for the ortho proton resonances of pyridine after formation of 9 (see Table 1).
104. β protons for diamagnetic metalloporphyrins usually increase with the oxidation state of the metal ions: a) See ref. [13f];
105. b) H. Scheer, J. J. Katz in Porphyrins and Metalloporphyrins (Ed.: K. M. Smith), Elsevier, Amsterdam, 1975, p. 460.
106. β chemical shuts (δ = 8.6 - 8.9).
107. 2- =meso-tetraphenylporphyrinato.
108. 2].
109. A. Antipas, J. W. Buchler, M. Gouterman, P. D. Smith, J. Am. Chem. Soc. 1978, 100, 3015.
110. Z.-Y. Li, J.-S. Huang, M. C.-W. Chan, K.-K. Cheung, C.-M. Che, Inorg. Chem. 1997, 36, 3064.
111. 2 =octaethylporphyrinato.
112. N. Li, V. Petricek, P. Coppens, J. Landrum, Acta Cryst. 1985, C41, 902.
113. W. R. Scheldt, Y. J. Lee, Struct. Bonding (Berlin) 1987, 64, 1.
114. 1H NMR measurements.
115. tpy = 2,2′:6,2″-terpyridine.
116. a) H. Irngartinger, W. Götzmann, Angew. Chem. 1986, 98, 359; Angew. Chem. Int. Ed. Engl. 1986, 25, 340;
117. a) H. Irngartinger, W. Götzmann, Angew. Chem. 1986, 98, 359; Angew. Chem. Int. Ed. Engl. 1986, 25, 340;
118. b) B. Bildstein, M. Schweiger, H. Kopacka, K.-H. Ongania, K. Wurst, Organometallics 1998, 17, 2414.
119. 2 6.70 (t, 4H), 6.55 (t, 8H), 3.81 (d, 8H).
120. a) H. Masuda, T. Taga, K. Osaki, H. Sugimoto, M. Mori, H. Ogoshi, J. Am. Chem. Soc. 1981, 103, 2199;
121. b) H. Masuda, T. Taga, K. Osaki, H. Sugimoto, M. Mori, H. Ogoshi, Bull. Chem. Soc. Jpn. 1982, 55, 3887;
122. c) J. P. Collman, C. E. Barnes, P. J. Brothers, T. J. Collins, T. Ozawa, J. C. Gallucci, J. A. Ibers, J. Am. Chem. Soc. 1984, 106, 5151.
123. D. D. Perrin, W. L. F. Armarego, D. R. Perrin, Purification of Laboratory Chemicals, Pergamon, Oxford, 1966, p. 273.
124. a) J. T. Groves, R. Quinn, Inorg. Chem. 1984, 23, 3844;
125. b) W.-H. Leung, C-M. Che, Am. Chem. Soc. 1989, 111, 8812;
126. C. Ho, W.-H. Leung, C.-M. Che, J. Chem. Soc. Dalton Trans. 1991, 2933.
127. D. P. Rillema, J. K. Nagle, L. F. Barringer, Jr., T. J. Meyer, J. Am. Chem. Soc. 1981, 103, 56.
128. DENZO: In The HKL Manual - A Description of Programs DENZO, XDISPLAYF, and SCALEPACK written by D. Gewirth with the cooperation of the program authors Z. Otwinowski, W. Minor, Yale University, New Haven (USA), 1995.
129. PATTY: P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, S. Garcia-Granda, R. O. Gould, J. M. M. Smits, C. Smykalla, The DIRDIF Program System, Technical Report of the Crystallography Laboratory, University of Nijmegen (The Netherlands), 1992.
130. SIR 92: A. Altomare, M. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Cryst. 1994, 27, 435.
131. TeXsan: Crystal Structure Analysis Package, Molecular Structure Corporation, The Woodlands, Texas (USA), 1985 & 1992.