Synthesis, structure and reactivity of iridium hydrido fluorido complexes

European Journal of Inorganic Chemistry

Volumn , Issue 9, 2012, Pages 1430-1436

  Kläring, Paul ^a   Jungton, Ann Katrin ^a   Braun, Thomas ^a   Müller, Carsten ^b  

^a HUMBOLDT UNIVERSITY   (Germany)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Fluorinated ligands; Fluorination; Hydride ligands; Iridium

Indexed keywords

CHELATION; CHLORINE COMPOUNDS; IRIDIUM COMPOUNDS; LIGANDS; SILICON COMPOUNDS; SYNTHESIS (CHEMICAL);

ACETYL CHLORIDE; ADDITION OF HF; CARBONYL COMPLEXES; FLUORINATED LIGANDS; FLUORINATING AGENTS; HYDRIDE LIGANDS; OXIDATIVE ADDITIONS; PYRAMIDAL CONFIGURATION;

FLUORINE COMPOUNDS;

EID: 84857588807     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201100917     Document Type: Article

References (120)

1. N. M. Doherty, N. W. Hoffman, Chem. Rev. 1991, 91, 553-573.
2. E. F. Murphy, R. Murugavel, H. W. Roesky, Chem. Rev. 1997, 97, 3425-3468.
3. H. W. Roesky, I. Haiduc, J. Chem. Soc., Dalton Trans. 1999, 2249-2264.
4. A. Mezzetti, C. Becker, Helv. Chim. Acta 2002, 85, 2686-2703.
5. V. V. Grushin, Acc. Chem. Res. 2010, 43, 160-171.
6. J. L. Kiplinger, T. G. Richmond, C. E. Osterberg, Chem. Rev. 1994, 94, 373-431.
7. J. Burdeniuc, B. Jedlicka, R. H. Crabtree, Chem. Ber./Recueil 1997, 130, 145-154.
8. T. G. Richmond, Angew. Chem. 2000, 112, 3378-3380; Angew. Chem. Int. Ed. 2000, 39, 3241 -3244.
9. T. Braun, R. N. Perutz, Chem. Commun. 2002, 2749-2757.
10. W. D. Jones, Dalton Trans. 2003, 3991-3995.
11. U. Mazurek, H. Schwarz, Chem. Commun. 2003, 1321-1326.
12. H. Torrens, Coord. Chem. Rev. 2005, 249, 1957-1985.
13. R. N. Perutz, T. Braun, Comprehensive Organometallic Chemistry III, Vol. 1 (Eds.:, R. H. Crabtree, M. P. Mingos), Elsevier, Oxford, 2007, p. 725.
14. H. Amii, K. Uneyama, Chem. Rev. 2009, 109, 2119-2183.
15. G. Meier, T. Braun, Angew. Chem. 2009, 121, 1575-1577; Angew. Chem. Int. Ed. 2009, 48, 1546 -1548.
16. R. P. Hughes, Eur. J. Inorg. Chem. 2009, 4591-4606.
17. T. G. Driver, Angew. Chem. 2009, 121, 8116-8119; Angew. Chem. Int. Ed. 2009, 48, 7974 -7976.
18. A. D. Sun, J. A. Love, Dalton Trans. 2010, 39, 10362-10374.
19. T. Braun, F. Wehmeier, Eur. J. Inorg. Chem. 2011, 613-625.
20. E. Clot, O. Eisenstein, N. Jasim, S. A. Macgregor, J. E. McGrady, R. N. Perutz, Acc. Chem. Res. 2011, 44, 333-348.
21. E. M. Carreira, B. L. Pagenkopf, Chem. Eur. J. 1999, 5, 3437-3442.
22. V. V. Grushin, Chem. Eur. J. 2002, 8, 1007-1014.
23. C. Bobbio, V. Gouverneur, Org. Biomol. Chem. 2006, 4, 2065-2075.
24. T. Furuya, J. E. M. N. Klein, T. Ritter, Synthesis 2010, 11, 1804-1821.
25. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147-1169.
26. T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470-477.
27. J. M. Brown, V. Gouverneur, Angew. Chem. 2009, 121, 8762-8766; Angew. Chem. Int. Ed. 2009, 48, 8610 -8614.
28. L. Hintermann, F. Läng, P. Maire, A. Togni, Eur. J. Inorg. Chem. 2006, 1396-1412.
29. K. L. Hull, W. Q. Anani, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 7134-7135.
30. J. A. Akana, K. X. Bhattacharyya, P. Müller, J. P. Sadighi, J. Am. Chem. Soc. 2007, 129, 7736-7737.
31. T. Furuya, H. M. Kaiser, T. Ritter, Angew. Chem. 2008, 120, 6082-6085; Angew. Chem. Int. Ed. 2008, 47, 5993 -5996.
32. T. Furuya, T. Ritter, J. Am. Chem. Soc. 2008, 130, 10060-10061.
33. X. Wang, T.-S. Mei, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 7520-7521.
34. W. Wang, J. Jasinski, G. B. Hammond, B. Xu, Angew. Chem. 2010, 122, 7405-7410; Angew. Chem. Int. Ed. 2010, 49, 7247 -7252.
35. C. Hollingworth, A. Hazari, M. N. Hopkinson, M. Tredwell, E. Benedetto, M. Huiban, A. D. Gee, J. M. Brown, V. Gouverneur, Angew. Chem. 2011, 123, 2661-2665; Angew. Chem. Int. Ed. 2011, 50, 2613 -2617.
36. J. E. Veltheer, P. Burger, R. G. Bergman, J. Am. Chem. Soc. 1995, 117, 12478-12488.
37. P. Barthazy, L. Hintermann, R. M. Stoop, M. Wörle, A. Mezzetti, A. Togni, Helv. Chim. Acta 1999, 82, 2448-2453.
38. P. Barthazy, R. M. Stoop, M. Wörle, A. Togni, A. Mezzetti, Organometallics 2000, 19, 2844-2852.
39. P. Barthazy, A. Togni, A. Mezzetti, Organometallics 2001, 20, 3472-3477.
40. W. J. Marshall, V. V. Grushin, Organometallics 2003, 22, 555-562.
41. V. V. Grushin, W. J. Marshall, J. Am. Chem. Soc. 2004, 126, 3068-3069.
42. W. J. Marshall, V. V. Grushin, Organometallics 2004, 23, 3343-3347.
43. S. A. McGregor, D. C. Roe, W. J. Marshall, K. M. Bloch, V. I. Bakhmutov, V. V. Grushin, J. Am. Chem. Soc. 2005, 127, 15304-15321.
44. D. V. Yandulov, N. T. Tran, J. Am. Chem. Soc. 2007, 129, 1342-1358.
45. V. V. Grushin, W. J. Marshall, Organometallics 2007, 26, 4997-5002.
46. T. Furuya, T. Ritter, J. Am. Chem. Soc. 2008, 130, 10060-10061.
47. A. W. Kaspi, A. Yahav-Levi, I. Goldberg, A. Vigalok, Inorg. Chem. 2008, 47, 5-7.
48. N. D. Ball, M. S. Sanford, J. Am. Chem. Soc. 2009, 131, 3796-3797.
49. D. A. Watson, M. Su, G. Teverovkiy, Y. Zhang, J. Garzía-Fortanet, T. Kinzel, S. L. Buchwald, Science 2009, 325, 1661-1664.
50. M. Reinhold, J. E. McGrady, R. N. Perutz, J. Am. Chem. Soc. 2004, 126, 5268-5276.
51. N. A. Jasim, R. N. Perutz, A. C. Whitwood, T. Braun, J. Izundu, B. Neumann, S. Rothfeld, H.-G. Stammler, Organometallics 2004, 23, 6140-6149.
52. A. Steffen, M. I. Sladek, T. Braun, B. Neumann, H.-G. Stammler, Organometallics 2005, 24, 4057-4064.
53. S. Burling, P. I. P. Elliott, N. A. Jasim, R. J. Lindup, J. McKenna, R. N. Perutz, S. J. Archibald, A. C. Whitwood, Dalton Trans. 2005, 3686-3695.
54. T. Schaub, M. Backes, U. Radius, J. Am. Chem. Soc. 2006, 128, 15964-159645.
55. T. Braun, J. Izundu, A. Steffen, B. Neumann, H.-G. Stammler, Dalton Trans. 2006, 5118-5123.
56. T. Wang, B. J. Alfonso, J. A. Love, Org. Lett. 2007, 9, 5629-5631.
57. T. Schaub, P. Fischer, A. Steffen, T. Braun, U. Radius, A. Mix, J. Am. Chem. Soc. 2008, 130, 9304-9317.
58. S. A. Johnson, C. W. Huff, F. Mustafa, M. Saliba, J. Am. Chem. Soc. 2008, 130, 17278-17280.
59. A. Nova, S. Erhardt, N. A. Jasim, R. N. Perutz, S. A. Macgregor, J. E. McGrady, A. C. Whitwoord, J. Am. Chem. Soc. 2008, 130, 15490-15498.
60. T. Wang, J. A. Love, Organometallics 2008, 27, 3290-3296.
61. H. L. Buckley, A. D. Sun, J. A. Love, Organometallics 2009, 28, 6622-6624.
62. H. L. Buckley, T. Wang, O. Tran, J. A. Love, Organometallics 2009, 28, 2356-2359.
63. S. A. Johnson, E. T. Taylor, S. J. Cruise, Organometallics 2009, 28, 3842-3655.
64. M. E. Doster, S. A. Johnson, Angew. Chem. 2009, 121, 2219-2221; Angew. Chem. Int. Ed. 2009, 48, 2185 -2187.
65. A. Nova, M. Reinhold, R. N. Perutz, S. A. Macgregor, J. E. McGrady, Organometallics 2010, 29, 1824-1831.
66. M. R. Cargill, G. Sandford, A. J. Tadeusiak, D. S. Yufit, J. A. K. Howard, P. Kilickiran, G. Nelles, J. Org. Chem. 2010, 75, 5860-5866.
67. D. Breyer, T. Braun, A. Penner, Dalton Trans. 2010, 39, 7513-7520.
68. A. J. Blake, R. W. Cockman, E. A. V. Ebsworth, J. H. Holloway, J. Chem. Soc., Chem. Commun. 1988, 529-530.
69. E. A. V. Ebsworth, N. Robertson, L. J. Yellowlees, J. Chem. Soc., Dalton Trans. 1993, 1031-1038.
70. S. A. Brewer, K. S. Coleman, J. Fawcett, J. H. Holloway, E. G. Hope, D. R. Russell, P. G. Watson, J. Chem. Soc., Dalton Trans. 1995, 1073-1076.
71. A. Yahav, I. Goldberg, A. Vigalok, J. Am. Chem. Soc. 2003, 125, 13634-13635.
72. A. Yahav, I. Goldberg, A. Vigalok, Inorg. Chem. 2005, 44, 1547-1553.
73. A. W. Kaspi, A. Yahav, I. Goldberg, A. Vigalok, Inorg. Chem. 2008, 47, 5-7.
74. T. Furuya, T. Ritter, J. Am. Chem. Soc. 2008, 130, 10060-10061.
75. J. Fawcett, D. A. J. Harding, E. G. Hope, Dalton Trans. 2010, 39, 5827-5832.
76. K. S. Coleman, J. Fawcett, J. H. Holloway, E. G. Hope, R. Nassar, J. Fluorine Chem. 2001, 112, 185-189.
77. K. Seppelt, Inorg. Chem. 2003, 42, 7116-7122.
78. K. S. Coleman, J. H. Holloway, E. G. Hope, J. Langer, J. Chem. Soc., Dalton Trans. 1997, 39, 4555-4559.
79. J. Gil-Rubio, B. Weberndörfer, H. Werner, J. Chem. Soc., Dalton Trans. 1999, 1437-1444.
80. M. Gorol, N. C. Mösch-Zanetti, H. W. Roesky, M. Noltemeyer, H.-G. Schmidt, Eur. J. Inorg. Chem. 2004, 2678-2682.
81. A. C. Cooper, K. Folting, J. C. Huffman, K. G. Caulton, Organometallics 1997, 16, 505-507.
82. C. Becker, I. Kieltsch, D. Broggini, A. Mezzetti, Inorg. Chem. 2003, 42, 8417-8429.
83. C. J. Bourgeois, S. A. Garratt, R. P. Hughes, R. B. Larichev, J. M. Smith, A. J. Ward, S. Willemsen, D. Zhang, A. G. DiPasquale, L. N. Zakharov, A. L. Rheingold, Organometallics 2006, 25, 3474-3480.
84. V. V. Grushin, W. J. Marshall, J. Am. Chem. Soc. 2006, 128, 12644-12645.
85. V. V. Grushin, W. J. Marshall, J. Am. Chem. Soc. 2009, 131, 918-919.
86. T. Furuya, D. Benitez, E. Tkatchouk, A. E. Strom, P. Tang, W. A. Goddard, T. Ritter, J. Am. Chem. Soc. 2010, 132, 3793-3807.
87. N. D. Ball, J. W. Kampf, M. S. Sanford, Dalton Trans. 2010, 39, 632-640.
88. A. Rossin, M. Peruzzini, F. Zanobini, Dalton Trans. 2011, 40, 4447-4452.
89. M. Ahijado Salomon, T. Braun, I. Krossing, Dalton Trans. 2008, 5197-5206.
90. P. Kläring, S. Pahl, T. Braun, A. Penner, Dalton Trans. 2011, 40, 6785-6791.
91. For a possible hydrolysis of fluorido complexes, see:, M. C. Pilon, V. V. Grushin, Organometallics 1998, 17, 1774-1781.
92. M. Ahijado, T. Braun, Angew. Chem. 2008, 120, 2996-3000; Angew. Chem. Int. Ed. 2008, 47, 2954 -2958.
93. G. Meier, T. Braun, Angew. Chem. 2011, 123, 3338-3342; Angew. Chem. Int. Ed. 2011, 50, 3380 -3384.
94. M. Ahijado Salomon, A.-K. Jungton, T. Braun, Dalton Trans. 2009, 7669-7677.
95. M. Ahijado Salomon, T. Braun, A. Penner, Angew. Chem. 2008, 120, 8999-9003; Angew. Chem. Int. Ed. 2008, 47, 8867 -8871.
96. J. Fawcett, D. A. J. Harding, E. G. Hope, K. Singh, G. A. Solan, Dalton Trans. 2010, 39, 10781-10789.
97. J. Choi, D. Y. Wang, S. Kundu, Y. Choliy, T. J. Emge, K. Krogh-Jespersen, A. S. Goldman, Science 2011, 332, 1545-1548.
98. G. Socrates, Infrared and Raman Characteristic Group Frequencies, Wiley, 2001, New York, p. 305.
99. A. W. Addison, T. N. Rao, J. Reedijk, J. van Rijn, G. C. Verschoor, J. Chem. Soc., Dalton Trans. 1984, 1349-1356.
100. D. Noveski, T. Braun, B. Neumann, A. Stammler, H.-G. Stammler, Dalton Trans. 2004, 4106-4119.
101. T. Braun, D. Noveski, M. Ahijado, F. Wehmeier, Dalton Trans. 2007, 3820-5125.
102. M. Teltewskoi, J. A. Panetier, S. A. Macgregor, T. Braun, Angew. Chem. 2010, 122, 4039-4043; Angew. Chem. Int. Ed. 2010, 49, 3947 -3951.
103. A. S. Goldman, J. Halpern, J. Organomet. Chem. 1990, 382, 37-253.
104. D. Noveski, T. Braun, M. Schulte, B. Neumann, H.-G. Stammler, Dalton Trans. 2003, 4075-4083.
105. M. Aizenberg, D. Milstein, Science 1994, 265, 359-361.
106. T. Braun, F. Wehmeier, K. Altenhöner, Angew. Chem. 2007, 119, 5415-5418; Angew. Chem. Int. Ed. 2007, 46, 5321 -5324.
107. M. F. Kühnel, D. Lentz, Angew. Chem. 2010, 122, 2995-2998; Angew. Chem. Int. Ed. 2010, 49, 2933 -2936.
108. D. Noveski, T. Braun, S. Krückemeier, J. Fluorine Chem. 2003, 125, 959-966.
109. C. Blankenship, S. E. Cremer, J. Organomet. Chem. 1989, 371, 19-30.
110. P. D. Lickiss, R. Lucas, J. Organomet. Chem. 1996, 510, 167-172.
111. O. Farooq, J. Chem. Soc. Perkin Trans. 1 1998, 661-665.
112. R. J. Lindup, T. B. Marder, R. N. Perutz, A. C. Whitwood, Chem. Commun. 2007, 3664-3666.
113. L. J. Krause, J. A. Morrison, J. Am. Chem. Soc. 1981, 103, 2995-3001.
114. A. Haas, T. Maciej, J. Fluorine Chem. 1982, 20, 581-588.
115. W. Dmowski, M. Kaminski, J. Fluorine Chem. 1983, 23, 219-228.
116. P. E. Hansen, F. M. Nicolaisen, K. Schaumburg, J. Am. Chem. Soc. 1986, 108, 625-629.
117. I. D. Gridnev, A. V. Shastin, E. S. Balenkova, Tetrahedron 1991, 47, 5577-5584.
118. R. Wagner, B. Wiedel, W. Guenther, H. Goerls, E. Anders, Eur. J. Org. Chem. 1999, 9, 2383-2390.
119. SHELXTL-PLUS, Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA, 1990;, G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112.
120. G. Cascarano, A. Altomare, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, D. Sigli, M. C. Burla, G. Polidori, M. Camalli, Acta Crystallogr., Sect. A 1996, 52, C79.