Aqueous transformation of a metal diformate to a metal dihydride carbonyl complex accompanied by H2 evolution from the formato ligands

Organometallics

Volumn 24, Issue 20, 2005, Pages 4816-4823

  Ogo, Seiji ^a   Nishida, Hiromi ^a   Hayashi, Hideki ^a   Murata, Yusuke ^a   Fukuzumi, Shunichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; CRYSTALLIZATION; IONIZATION; MASS SPECTROMETRY; ORGANOMETALLICS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

AQUEOUS TRANSFORMATION; DIMETHYL SULFOXIDE (DMSO); METAL DIFORMATE; METAL DIHYDRIDE CARBONYL COMPLEX;

RHODIUM COMPOUNDS;

EID: 26444521577     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0504147     Document Type: Article

References (114)

1. (a) Matsuoka, S.; Yamamoto, K.; Ogata, T.; Kusaba, M.; Nakashima, N.; Fujita, E.; Yanagida, S. J. Am. Chem. Soc. 1993, 115, 601-609.
2. (b) Fujita, E.; Brunschwig, B. S.; Ogata, T.; Yanagida, S. Coord. Chem. Rev. 1994, 132, 195-200.
3. (c) Ogata, T.; Yanagida, S.; Brunschwig, B. S.; Fujita, E. J. Am. Chem. Soc. 1995, 117, 6708-6716.
4. (d) Dhanasekaran, T.; Grodkowski, J.; Neta, P.; Hambright, P.; Fujita, E. J. Phys. Chem. A 1999, 103, 7742-7748.
5. (a) Ogata, T.; Yamamoto, Y.; Wada, Y.; Murakoshi, K.; Kusaba, M.; Nakashima, N.; Ishida, A.; Takamuku, S.; Yanagida, S. J. Phys. Chem. 1995, 99, 11916-11922.
6. (b) Willner, I.; Maidan, R.; Mandler, D.; Dürr, H.; Dörr, G.; Zengerle, K. J. Am. Chem. Soc. 1987, 109, 6080-6086.
7. (c) Teramura, K.; Tanaka, T.; Ishikawa, H.; Kohno, Y.; Funabiki, T. J. Phys. Chem. B 2004, 108, 346-354.
8. (a) Behar, D.; Dhanasekaran, T.; Neta, P.; Hosten, C. M.; Ejeh, D.; Hambright, P.; Fujita, E. J. Phys. Chem. A 1998, 102, 2870-2877.
9. (b) Hori, Y.; Takahashi, R.; Yoshinami, Y.; Murata, A. J. Phys. Chem. B 1997, 101, 7075-7081.
10. Maiella, P. G.; Brill, T. B. J. Phys. Chem. A 1998, 102, 5886-5891.
11. (a) Zhouo, Z.; Shi, Y.; Zhang, H.; Zhou, X.; Fu, H. J. Mol. Struct. (THEOCHEM)2004, 682, 1-7.
12. (b) Wang, B.; Hou, H.; Gu, Y. J. Phys. Chem. A 2000, 104, 10526-10528.
13. (a) Markovic, N. M.; Ross, P. N. Surf. Sci. Rep. 2002, 45, 117-229.
14. (b) Arenz, M.; Stamenkovic, V.; Ross, P. N.; Markovic, N. M. Surf. Sci. 2004, 573, 57-66.
15. (a) Thomas, F. S.; Masel, R. I. Surf. Sci. 2004, 573, 169-175.
16. (b) Columbia, M. R.; Thiel, P. A. J. Electroanal. Chem. 1994, 369, 1-14.
17. (c) Parsons, R.; VanderNoot, T. J. Electroanal. Chem. 1988, 257, 9-45.
18. Hu, S.-W.; Lü, S.-M.; Wang, X.-Y. J. Phys. Chem. A 2004, 108, 8485-8494.
19. (a) Adschiri, T.; Shibata, R.; Sato, T.; Watanabe, M.; Arai, K. Ind. Eng. Chem. Res. 1998, 37, 2634-2638.
20. (b) Sato, T.; Kurosawa, S.; Smith, R. L., Jr.; Adschiri, T.; Arai, K. J. Supercrit. Fluids 2004, 29, 113-119.
21. (a) Yoshida, K.; Wakai, C.; Matubayashi, N.; Nakahara, M. J. Phys. Chem. A 2004, 108, 7479-7482.
22. (b) Kruse, A.; Dinjus, E. Angew. Chem., Int. Ed. 2003, 42, 909-911.
23. (a) Cabilla, G. C.; Bonivardi, A. L.; Baltanás, M. A. Appl. Catal. A: Gen. 2003, 255, 181-195.
24. (b) Miksa, D.; Brill, T. B. Ind. Eng. Chem. Res. 2001, 40, 3098-3103.
25. Laine, R. M.; Rinker, R. G.; Ford, P. C. J. Am. Chem. Soc. 1977, 99, 252-253.
26. (a) Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1995, 95, 259-272.
27. (b) Leitner, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2207-2221.
28. (a) Hayashi, H.; Ogo, S.; Abura, T.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 14266-14267.
29. (b) Hayashi, H.; Ogo, S.; Fukuzumi, S. Chem. Commun. 2004, 2714-2715.
30. (a) Angoletta, M.; Malatesta, L.; Caglio, G. J. Organomet. Chem. 1975, 94, 99-106.
31. (b) Rang, H.; Mauldin, C. H.; Cole, T.; Slegeir, W.; Cann, K.; Pettit, R. J. Am. Chem. Soc. 1977, 99, 8323-8325.
32. (c) Slegeir, W. A. R.; Sapienza, R. S.; Rayford, R.; Lam, L. Organometallics 1982, 1, 1728-1730.
33. (d) Weiller, B. H.; Liu, J.-P.; Grant, E. R. J. Am. Chem. Soc. 1985, 107, 1595-1604.
34. (e) Funaioli, T.; Biagini, P.; Fachinetti, G. Inorg. Chem. 1990, 29, 9, 1440-1442.
35. (f) Tsai, J.-C.; Khan, M. A.; Nicholas, K. M. Organometallics 1991, 10, 29-30.
36. (g) Ziessel, R. J. Am. Chem. Soc. 1993, 115, 118-127.
37. (h) Torrent, M.; Solà, M.; Frenking, G. Organometallics 1999, 18, 2801-2812.
38. (i) King, R. B. J. Organomet. Chem. 1999, 586, 2-17.
39. (k) Barrows, S. E. Inorg. Chem. 2004, 43, 8236-8238.
40. (a) Cheng, C.-H.; Hendriksen, D. E.; Eisenberg, R. J. Am. Chem. Soc. 1977, 99, 2791-2792.
41. (b) Cheng, C.-H.; Eisenberg, R. J. Am. Chem. Soc. 1978, 100, 5968-5970.
42. (c) Baker, E. C.; Hendriksen, D. E.; Eisenberg, R. J. Am. Chem. Soc. 1980, 102, 1020-1027.
43. (a) Ford, P. C.; Rinker, R. G.; Ungermann, C.; Laine, R. M.; Landis, V.; Moya, S. A. J. Am. Chem. Soc. 1978, 100, 4595-4597.
44. (b) Ungermann, C.; Landis, V.; Moya, S. A.; Cohen, H.; Walker, H.; Pearson, R. G.; Rinker, R. G.; Ford, P. C. J. Am. Chem. Soc. 1979, 101, 5922-5929.
45. (c) Ford, P. C. Acc. Chem. Res. 1981, 14, 31-37.
46. (d) Gross, D. C.; Ford, P. C. J. Am. Chem. Soc. 1985, 107, 585-593.
47. (e) Trautman, R. J.; Gross, D. C.; Ford, P. C. J. Am. Chem. Soc. 1985, 107, 2355-2362.
48. (f) Pardey, A. J.; Ford, P. C. J. Mol. Catal. 1989, 53, 247-263.
49. (a) King, R. B.; Frazier, C. C.; Hanes, R. M.; King, A. D., Jr. J. Am. Chem. Soc. 1978, 100, 2925-2927.
50. (b) King, A. D., Jr.; King, R. B.; Yang, D. B. J. Am. Chem. Soc. 1980, 102, 1028-1032.
51. (c) King, A. D., Jr.; King, R. B.; Sailers, E. L., III. J. Am. Chem. Soc. 1981, 103, 1867-1868.
52. (d) King, A. D., Jr.; King, R. B.; Yang, D. B. J. Am. Chem. Soc. 1981, 103, 2699-2704.
53. (a) Yoshida, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3941-3942.
54. (b) Yoshida, T.; Okano, T.; Otsuka, S. J. Am. Chem. Soc. 1980, 102, 5966-5967.
55. (c) Yoshida, T.; Okano, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1981, 103, 3411-3422.
56. (a) Bricker, J. C.; Nagel, C. C.; Shore, S. G. J. Am. Chem. Soc. 1982, 104, 1444-1445.
57. (b) Bricker, J. C.; Nagel, C. C.; Bhattacharyya, A. A.; Shore, S. G. J. Am. Chem. Soc. 1985, 107, 377-384.
58. (a) Darensbourg, D. J.; Baldwin, B. J.; Froelich, J. A. J. Am. Chem. Soc. 1980, 102, 4688-4694.
59. (b) Darensbourg, D. J.; Rokicki, A.; Darensbourg, M. Y. J. Am. Chem. Soc. 1981, 103, 3223-3224.
60. (c) Darensbourg, D. J.; Ovalles, C. J. Am. Chem. Soc. 1987, 109, 3330-3336.
61. (a) Lane, K. R.; Lee, R. E.; Sallans, L.; Squires, R. R. J. Am. Chem. Soc. 1984, 106, 5767-5772.
62. (b) Sunderlin, L. S.; Squires, R. R. J. Am. Chem. Soc. 1993, 115, 337-343.
63. (a) Taqui-Khan, M. M.; Halligudi, S. B.; Rao, N. N.; Shukla, S. J. Mol. Catal. 1989, 51, 161-170.
64. (b) Taqui-Khan, M. M.; Halligudi, S. B.; Shukla, S. J. Mol. Catal. 1989, 57, 47-60.
65. (a) Jenner, G.; Nahmed, E. M.; Leismann, H. J. Organomet. Chem. 1990, 387, 315-321.
66. (b) Jenner, G.; Nahmed, E. M.; Libs-Konrath, S. J. Mol. Catal. 1991, 64, 337-347.
67. (a) Ogo, S.; Abura, T.; Watanabe, Y. Organometallics 2002, 21, 2964-2969.
68. (b) Abura, T.; Ogo, S.; Watanabe, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 4149-4154.
69. Reviews: (a) Joó, F. Catalysis by Metal Complexes; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2001; Vol. 23, Aqueous Organometallic Catalysis, pp 113-122, and references therein.
70. (b) Leitner, W.; Dinjus, E.; Gassner, F. In Aqueous-Phase Organometallic Catalysis, Concepts and Applications; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 486-498, and references therein.
71. (c) Behr, A. Carbon Dioxide Activation by Metal Complexes; VCH: Weinheim, Germany, 1988, and references therein.
72. Strauss, S. H.; Whitmire, K. H.; Shriver, D. F. J. Organomet. Chem. 1979, 174, C59-C62.
73. (a) Khai, B. T.; Arcelli, A. J. Organomet. Chem. 1986, 309, C63-C66.
74. (b) Tsai, J.-C.; Nicholas, K. M. J. Am. Chem. Soc. 1992, 114, 5117-5124.
75. (c) Onishi, M. J. Mol. Catal. 1993, 80, 145-149.
76. Gao, Y.; Kuncheria, J.; Yap, G. P. A.; Puddephatt, R. J. Chem. Commun. 1998, 2365-2366.
77. (e) Man, M. L.; Zhou, Z.; Ng, S. M.; Lau, C. P. Dalton Trans. 2003, 3727-3735.
78. Ruelle, P.; Kesselring, U. W.; Nam-Tran, H. J. Am. Chem. Soc. 1986, 108, 371-375.
79. (a) Watanabe, M.; Sato, T.; Inomata, H.; Smith, R. L., Jr.; Arai, K.; Kruse, A.; Dinjus, E. Chem. Rev. 2004, 104, 5803-5821.
80. (b) Yagasaki, T.; Saito, S.; Ohmine, I. J. Chem. Phys. 2002, 117, 7631-7639.
81. (c) Wakai, C.; Yoshida, K.; Tsujino, Y.; Matubayasi, N.; Nakahara, M. Chem. Lett. 2004, 33, 572-573.
82. (d) Osada, M.; Watanabe, M.; Sue, K.; Adschiri, T.; Arai, K. J. Supercrit. Fluids 2004, 28, 219-224.
83. (a) Solymosi, F.; Kiss, J.; Kovács, I. J. Phys. Chem. 1988, 92, 796-803.
84. (b) Iglesia, E.; Boudart, M. J. Phys. Chem. 1991, 95, 7011-7016.
85. (c) Onishi, H.; Aruga, T.; Iwasawa, Y. J. Am. Chem. Soc. 1993, 115, 10460-10461.
86. (d) Kubo, T.; Minami, N.; Aruga, T.; Takagi, N.; Nishijima, M. J. Phys. Chem. B 1997, 101, 7007-7011.
87. (e) Lu, G.-Q.; Crown, A.; Wieckowski, A. J. Phys. Chem. B 1999, 103, 9700-9711.
88. (f) Arenz, M.; Stamenkovic, V.; Schmidt, T. J.; Wandelt, K.; Ross, P. N.; Markovic N. M. Phys. Chem. Chem. Phys. 2003, 5, 4242-4251.
89. (g) Yamakata, A.; Kubota, J.; Kondo, J. N.; Hirose, C.; Domen, K.; Wakabayashi, F. J. Phys. Chem. B 1997, 101, 5177-5181.
90. (a) Fujita, E.; Chou, M.; Tanaka, K. Appl. Organomet. Chem. 2000, 14, 844-846.
91. (b) Tanaka, K.; Ooyama, D. Coord. Chem. Rev. 2002, 226, 211-218.
92. (a) Halpern, J.; Kemp, A. L. W. J. Am. Chem. Soc. 1966, 88, 5147-5150.
93. (b) Yi, C. S.; Liu, N. Organometallics 1995, 14, 2616-2617.
94. (c) Lindner, E.; Keppeler, B.; Wegner, P. Inorg. Chim. Acta 1997, 258, 97-100.
95. (d) Gao, Y.; Jennings, M. C.; Puddephatt, R. J. Organometallics 2001, 20, 1882-1888.
96. (e) Shin, J. H.; Churchill, D. G.; Parkin, G. J. Organomet. Chem. 2002, 642, 9-15.
97. (a) Kaska, W. C.; Nemeh, S.; Shirazl, A.; Potuznik, S. Organometallics 1988, 7, 13-15.
98. (b) McLoughlin, M. A.; Keder, N. L.; Harrison, W. T. A.; Flesher, R. J.; Mayer, H. A.; Kaska, W. C. Inorg. Chem. 1999, 38, 3223-3227.
99. Heterogeneous: (a) Ying, D. H. S.; Madix, R. J. Inorg. Chem. 1978, 17, 1103-1108.
100. (b) Xu, C.; Goodman, D. W. J. Phys. Chem. 1996, 100, 1753-1760.
101. Homogeneous: (a) Elliott, D. C.; Hallen, R. T.; Sealock, L. J., Jr. Ind. Eng. Chem. Prod. Res. Dev. 1983, 22, 431-435.
102. (b) Elliott, D. C.; Sealock, L. J., Jr.; Butner, R. S. Ind. Eng. Chem. Prod. Res. Dev. 1986, 25, 541-549.
103. A large excess of formic acid is required to isolate the dihydride CO complex 5, which contains two hydrido ligands.
104. Galsboel, F.; Petersen, C. H.; Simonsen, K. Acta Chem. Scand. 1996, 50, 567-570.
105. (a) Ogo, S.; Makihara, N.; Watanabe, Y. Organometallics 1999, 18, 5470-5474.
106. (b) Takara, S.; Ogo, S.; Watanabe, Y.; Nishikawa, K.; Kinoshita, I.; Isobe, K. Angew. Chem., Int. Ed. 1999, 38, 3051-3053.
107. Chen, P. Angew. Chem., Int. Ed. 2003, 42, 2832-2847.
108. Hayashi, H.; Nishida, H.; Ogo, S.; Fukuzumi, S. Inorg. Chim. Acta 2004, 357, 2939-2944.
109. 2 in nitrogenases has been pointed out: (a) Ogo, S.; Nakai, H.; Watanabe, Y. J. Am. Chem. Soc. 2002, 124, 597-601.
110. (b) Ogo, S.; Kure, B.; Nakai, H.; Watanabe, Y.; Fukuzumi, S. Appl. Organomet. Chem. 2004, 18, 589-594.
111. (c) Fryzuk, M. D.; MacKay, B. A.; Patrick, B. O. J. Am. Chem. Soc. 2003, 125, 3234-3235.
112. 2, see: (a) Brown, K. L.; Clark, G. R.; Headford, C. E. L.; Marsden, K.; Roper, W. R. J. Am. Chem. Soc. 1979, 101, 503-505.
113. (b) Thorn, D. L. Organometallics 1982, 1, 197-204. The exact mechanism of the hydrogen evolution remains to be further clarified.
114. Nakamoto, K. In Infrared and Raman Spectra of Inorganic and Coordination Compounds, 5th ed.; Wiley: New York, 1997, and references therein.