Preparation, characterization, and reactivity of azido complex containing a Tp( tBuNC)(PPh 3)Ru fragment and ruthenium-catalyzed cycloaddition of organic azides with alkynes in organic and aqueous media

Organometallics

Volumn 31, Issue 19, 2012, Pages 6887-6899

  Lo, Yih Hsing ^a   Wang, Tsang Hsiu ^a   Lee, Chia Yi ^a   Feng, Ying Hsuan ^a  

^a UNIVERSITY OF TAIPEI   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION PRODUCTS; AQUEOUS MEDIA; AQUEOUS MEDIUM; BONDING TYPE; CARBONYL COMPLEXES; CYCLOADDITIONS; FISCHER CARBENE COMPLEX; ISOTHIOCYANATES; LIGAND SUBSTITUTION REACTIONS; ORGANIC AZIDES; SODIUM AZIDE; TERMINAL ALKYNE; THERMALLY UNSTABLE;

ACETYLENE; BROMINE COMPOUNDS; CATALYSIS; CHLORINE COMPOUNDS; CYCLOADDITION; NITROGEN COMPOUNDS; RUTHENIUM; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

RUTHENIUM COMPOUNDS;

EID: 84867385337     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om300687a     Document Type: Article

References (117)

1. Nomiya, K.; Noguchi, R.; Oda, M. Inorg. Chim. Acta 2000, 298, 24
2. Singh, H.; Chawla, A. S.; Kapoor, V. K.; Paul, D.; Malhotra, R. Prog. Med. Chem. 1980, 17, 151
3. Fan, W. Q.; Katritzky, A. R. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, U.K., 1996; Vol. 4, pp 1-126.
4. Herr, R. J. Bioorg. Med. Chem. 2002, 10, 3379
5. Truica-Marasescu, F.; Wertheimer, M. R. Plasma Process. Polym. 2008, 5, 44
6. Katritzky, A. R.; Rees, C. W. Comprehensive Heterocyclic Chemistry; Pergamon Press: Elmsford, NY, 1984; Vol. 5, Part 4A, pp 791-838.
7. Szocs, E.; Bako, I.; Kosztolanyi, T.; Bertoti, I.; Kalman, E. Electrochim. Acta 2004, 49, 1371
8. Klapötke, T. M.; Mayer, P.; Sabaté, C. M.; Welch, J. M.; Wiegand, N. Inorg. Chem. 2008, 47, 6014
9. KlapÖotke, T. M.; Stierstorfer, J. J. Am. Chem. Soc. 2009, 131, 1122
10. Klapötke, T. M.; Sabaté, C. M.; Welch, J. M. Eur. J. Inorg. Chem. 2009, 769
11. Tao, G.-H.; Twamley, B.; Shreeve, J. M. Inorg. Chem. 2009, 48, 9918
12. Singh, R. P.; Verma, R. D.; Meshri, D. T.; Shreeve, J. M. Angew. Chem., Int. Ed. 2006, 45, 3584
13. Tappan, B. C.; Huynh, M. H.; Hiskey, M. A.; Chavez, D. E.; Luther, E. P.; Mang, J. T.; Son, S. F. J. Am. Chem. Soc. 2006, 128, 6589
14. Poturovic, S.; Lu, D.; Heeg, M. J.; Winter, C. H. Polyhedron 2008, 27, 3280
15. Huisgen, R. Proc. Chem. Soc. 1961, 357
16. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 565
17. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 633
18. Huisgen, R. J. Org. Chem. 1976, 41, 403
19. Fruhauf, H. W. Chem. Rev. 1997, 97, 523
20. Treichel, P. M.; Knebel, W. J.; Hess, R. W. J. Am. Chem. Soc. 1971, 93, 5424
21. Beck, W.; Burger, K.; Fehlhammer, W. P. Chem. Ber. 1971, 104, 1816
22. Fehlhammer, W. P.; Dahl, L. F. J. Am. Chem. Soc. 1972, 94, 3370
23. Fehlhammer, W. P.; Kemmerich, T.; Beck, W. Chem. Ber. 1979, 112, 468
24. Beck, W.; Fehlhammer, W. P. Angew. Chem., Int. Ed. Engl. 1967, 6, 169
25. Beck, W.; Fehlhammer, W. P.; Pollmann, P.; Schachl, H. Chem. Ber. 1969, 102, 1976
26. Beck, W.; Fehlhammer, W. P.; Bock, H.; Bander, M. Chem. Ber. 1969, 102, 3637
27. Beck, W.; Bander, M.; Fehlhammer, W. P.; Pohlmann, P.; Schachl, H. Inorg. Nucl. Chem. Lett. 1968, 4, 143
28. Washburne, S. S.; Peterson, W. R., Jr. J. Organomet. Chem. 1970, 21, 427
29. Sisido, K.; Nabika, K.; Isida, T.; Kozima, S. J. Organomet. Chem. 1971, 33, 337
30. Kemmerich, T.; Beck, W.; Spencer, C.; Mason, R. Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys., Biol. 1972, 27B, 745
31. Gaughan, A. P.; Browman, K. S.; Dori, Z. Inorg, Chem. 1972, 11, 601
32. Beck, W.; Schropp, K. Chem. Ber. 1975, 108, 3317
33. Rigby, W.; Bailey, P. M.; McCleverty, J. A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1979, 371
34. Gorth, H.; Henry, M. C. J. Organomet. Chem. 1967, 9, 117
35. Kozima, S.; Itano, T.; Mihara, N.; Sisido, K.; Isida, T. J. Organomet. Chem. 1972, 44, 117
36. Erbe, J.; Beck, W. Chem. Ber. 1983, 116, 3867
37. Rosen, A.; Rosenblum, M. J. Organomet. Chem. 1974, 80, 103
38. Ziolo, R. F.; Dori, Z. J. Am. Chem. Soc. 1968, 90, 6560
39. Ziolo, R. F.; Thich, J. A.; Dori, Z. Inorg. Chem. 1972, 11, 626
40. Sato, F.; Etoh, M.; Sato, M. J. Organomet. Chem. 1974, 70, 101
41. Kreutzer, P. H.; Weis, J. C.; Bock, H.; Erbe, J.; Beck, W. Chem. Ber. 1983, 116, 2691
42. Ellis, W. R., Jr.; Purcell, W. L. Inorg. Chem. 1982, 21, 834
43. Hall, J. H.; De La Vega, R. L.; Purcell, W. L. Inorg. Chim. Acta 1985, 102, 157
44. Chang, C. C.; Lee, G. H. Organometallics 2003, 22, 3107
45. Govindaswamy, P.; Mobin, S. M.; Thöne, C.; Mohan Rao, K. J. Organomet. Chem. 2005, 690, 1218
46. Liu, F.-C.; Lin, Y.-L.; Yang, P.-S.; Lee, G. H.; Peng, S.-M. Organometallics 2010, 29, 4282
47. Cadierno, V.; Gamasa, M. P.; Gimeno, J. Coord. Chem. Rev. 2004, 248, 1627
48. Rigaut, S.; Touchard, D.; Dixneuf, P. H. Coord. Chem. Rev. 2004, 248, 1585
49. Guerchais, V. Eur. J. Inorg. Chem. 2002, 783
50. Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311
51. Puerta, M. C.; Valerga, P. Coord. Chem. Rev. 1999, 193-195, 977
52. Cadierno, V.; Diez, J.; Gamasa, M. P.; Gimeno, J.; Lastra, E. Coord. Chem. Rev. 1999, 193-195, 147
53. Bruce, M. I. Chem. Rev. 1998, 98, 2797
54. Touchard, D.; Dixneuf, P. H. Coord. Chem. Rev. 1998, 178-180, 409
55. Werner, H. J. Chem. Soc., Chem. Commun. 1997, 903
56. Bruce, M. I. Chem. Rev. 1991, 91, 197
57. Bernad, D. J.; Esteruelas, M. A.; Lopez, A. M.; Modrego, J.; Puerta, M. C.; Valerga, P. Organometallics 1999, 18, 4995
58. Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585
59. Barrett, G. M.; Carpenter, N. E. Organometallics 1987, 6, 2249
60. Ouzzine, K.; Le Bozec, H.; Dixneuf, P. H. J. Organomet. Chem. 1986, 317, C25
61. Gamasa, M. P.; Gimeno, J.; Gonzaleszcueva, M.; Lastra, E. J. Chem. Soc., Dalton Trans. 1996, 2547
62. Nombel, P.; Lugan, N.; Mathieu, R. J. Organomet. Chem. 1995, 503, C22
63. Bruce, M. I.; Swincer, A. G.; Wallis, R. C. J. Organomet. Chem. 1979, 171, C5
64. Pavlik, S.; Mereiter, K.; Puchberger, M.; Kirchner, K. Organometallics 2005, 24, 3561
65. Hu, T.-C.; Hsiao, P.-I.; Wang, T.-H.; Yang, Y.-W.; Chang, C.-Y.; Wu, Y.-H.; Sun, W.-C.; Yu, M.-S.; Lee, C.-Y.; Lo, Y.-H. Dalton Trans. 2011, 40, 12663
66. Lo, Y.-H.; Lin, Y.-C.; Lee, G.-H.; Wnag, Y. Organometallics 1999, 18, 982-988
67. Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Iglesias, L.; Garcia-Granda, S. Inorg. Chem. 1999, 38, 2874
68. Gamasa, M. P.; Gimeno, J.; Gonzalez-Bernardo, C.; Borge, J.; Garcia-Granda, S. Organometallics 1997, 16, 2483
69. Rüba, E.; Slugovc, C.; Gemel, C.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1999, 18, 2275
70. Bianchini, C.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1995, 14, 3152
71. Barrett, A. G. M.; Carpenter, N. E. Organometallics 1987, 6, 2249
72. Ouzzine, K.; Le Bozec, H.; Dixneuf, P. H. J. Organomet. Chem. 1986, 317, C25
73. Nombel, P.; Lugan, N.; Mathieu, R. J. Organomet. Chem. 1995, 503, C22
74. Le Bozec, H.; Ouzzine, K.; Dixneuf, P. H. Organometallics 1991, 10, 2768
75. Esteruelas, M. A.; Gomez, A. V.; Lopez, A. M.; Modrego, J.; Onate, E. Organometallics 1998, 17, 5434
76. Senn, D. R.; Wong, A.; Patton, A. T.; Marsi, M.; Strouse, C. E.; Gladysz, J. A. J. Am. Chem. Soc. 1988, 110, 6096
77. Ting, P. C.; Lin, Y. C.; Lee, G. H.; Cheng, M. C.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 6433
78. Nathaniel, W.; Alock, N. W.; Burns, I. D.; Claire, K. S.; Hill, A. F. Inorg. Chem. 1992, 31, 2906
79. Singleton, E.; Ooethuizen, H. E. Adv. Organomet. Chem. 1983, 22, 209
80. Busetto, L.; Palazzi, A.; Ros, R. Inorg. Chim. Acta 1975, 13, 233
81. Chen, C.-K.; Tong, H.-C.; Chen Hsu, C.-Y.; Lee, C.-Y.; Fong, Y.-S.; Chung, Y.-S.; Lo, Y.-H.; Lin, Y.-C.; Wang, Y. Organomtallics 2009, 28, 3358
82. Paul, P.; Nag, K. Inorg. Chem. 1987, 26, 2969
83. Nelson, J. H.; Schmitt, D. L.; Henty, R. A.; Moore, D. W.; Jonassen, H. B. Inorg. Chem. 1970, 9, 2678
84. Redfield, D. A.; Nelson, J. H.; Henry, R. A.; Moore, D. W.; Jonassen, H. B. J. Am. Chem. Soc. 1974, 96, 6298
85. Kieft, R. L.; Peterson, W. M.; Blundell, G. L.; Horton, S.; Henry, R. A.; Jonasson, H. B. Inorg. Chem. 1976, 15, 1721
86. Kemmerich, T.; Nelson, J. H.; Takach, N. E.; Boeheme, H.; Jablonski, B.; Beck, W. Inorg. Chem. 1982, 21, 1226
87. Singh, K. S.; Kreisel, K. A.; Yap, G. P.; Kollipara, M. R. J. Organomet. Chem. 2006, 691, 3509
88. Parashad, R.; Yadav, S. K. S.; Agarwala, U. J. Inorg. Nucl. Chem. 1981, 43, 2359
89. Rowley, M.; Steed, J. W.; Tocher, D. A. Polyhedron 1995, 14, 1415
90. Preetz, W.; Fricke, H. H. Z. Anorg. Allg. Chem. 1982, 486, 49
91. Poddar, R. K.; Parashad, R.; Agarwala, U. J. Inorg. Nucl. Chem. 1980, 42, 837
92. Kohle, O.; Ruile, S.; Grätzel, M. Inorg. Chem. 1996, 35, 4779
93. Homanen, P.; Haukka, M.; Pakkanen, T. A.; Pursiainen, J.; Laitinen, R. H. Organometallics 1996, 15, 4081
94. Tokunaga, M.; Suzuki, T.; Koga, N.; Fukushima, T.; Horiuchi, A.; Wakatsuki, Y. J. Am. Chem. Soc. 2001, 123, 11917
95. Grotjahn, D. B.; Lev, D. A. J. Am. Chem. Soc. 2004, 126, 12232
96. Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585
97. Le Bozec, H.; Ouzzine, K.; Dixneuf, P. H. Organometallics 1991, 10, 2768
98. Beddoes, R. L.; Grime, R. W.; Hussain, Z. I.; Whiteley, M. W. J. Organomet. Chem. 1996, 526, 371
99. Barthel-Rosa, L. P.; Maitra, K.; Fischer, J.; Nelson, J. H. Organometallics 1997, 16, 1714
100. Leung, W.-H.; Chan, E. Y. Y.; Williams, I. D.; Wong, W.-T. Organometallics 1997, 16, 3234
101. Hansen, H. D.; Nelson, J. H. Organometallics 2000, 19, 4740
102. Gamasa, M. P.; Gimeno, J.; Martín-Vaca, B. M.; Isea, R.; Vegas, A. J. Organomet. Chem. 2002, 651, 22
103. Keller, A.; Jasionka, B.; Gzowiak, T.; Ershov, A.; Matusiak, R. Inorg. Chim. Acta 2003, 344, 49
104. Pavlik, S.; Mereiter, K.; Puchberger, M.; Kirchner, K. J. Organomet. Chem. 2005, 690, 5497
105. Kopf, H.; Pietraszuk, C.; Hubner, E.; Burzlaff, N. Organometallics 2006, 25, 2533
106. Beddoes, R. L.; Grime, R. W.; Hussain, Z. I.; Whiteley, M. W. J. Organomet. Chem. 1996, 526, 371
107. Lo, Y.-H.; Chen, H.-G.; Kuo, T.-S. Dalton Trans. 2011, 40, 2711
108. Nagao, H.; Kikuchi, T.; Inukai, M.; Ueda, A.; Oi, T.; Suzuki, N.; Yamasaki, M. Angew. Chem., Int. Ed. 2006, 45, 3131
109. Albertin, G.; Antoniutti, S.; Giorgi, M. T. Eur. J. Inorg. Chem. 2003, 2855
110. Zhang, J.; Gunnoe, T. B.; Petersen, J. L. Inorg. Chem. 2004, 44, 2895
111. Garnovskii, D. A.; Pombeiro, A. J. L.; Haukka, M.; Sobota, P.; Kukushkin, V. Y. Dalton Trans. 2004, 1097
112. Milligan, D.; Jacox, M. E. J. Chem. Phys. 1963, 39, 712
113. Milligan, D. E. J. Chem. Phys. 1961, 35, 1491
114. Zhang, L.; Chen, X.; Xue, P.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G. J. Am. Chem. Soc. 2005, 127, 15998
115. Joo, F. Aqueous Organometallic Catalysis; Kluwer: Dordrecht, The Netherlands, 2001.
116. The SADABS program is based on the method of Blessing; see: Blessing, R. H. Acta Crystallogr., Sect. A 1995, 51, 33
117. SHELXTL: Structure Analysis Program, version 5.04; Siemens Industrial Automation Inc.: Madison, WI, 1995.