Organometallics CIF format. This material is available free <strong>of</strong> charge via the Internet ■ at http://pubs.acs.org. AUTHOR INFORMATION Corresponding Author *E-mail: jgr@um.es, http://www.um.es/gqo/. ■ ACKNOWLEDGMENTS We thank the Spanish Ministerio de Ciencia e Innovacioń (grant CTQ2007-60808/BQU, with FEDER support) and Fundacioń Seńeca (grants 02992/PI/05 and 04539/GERM/06) for financial support. ■ DEDICATION † DedicatedtoPr<strong>of</strong>.JuanFornieś on the occasion <strong>of</strong> his retirement. ■ REFERENCES (1) Engle, K. M.; Mei, T.-S.; Wang, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2011, 50, 1478. (2) Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475. (3) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470. (4) Morrison, J. A. Adv. Organomet. Chem. 1993, 35, 211. (5) Hughes, R. P. Adv. Organomet. Chem. 1990, 31, 183. (6) Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 12644. (7) Dubinina, G. G.; Brennessel, W. W.; Miller, J. L.; Vicic, D. A. Organometallics 2008, 27, 3933. (8) Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 2878. (9) Ye, Y.; Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 14682. (10) Ball, N. D.; Gary, J. B.; Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 7577. (11) Dolbier, W. R. Chem. Rev. 1996, 96, 1557. (12) Chen, Q.-Y.; Yang, Z.-Y. J. Fluorine Chem. 1988, 39, 217. (13) Xiao, F.; Wu, F.; Yang, X.; Shen, Y.; Shi, X. J. Fluorine Chem. 2005, 126, 319. (14) Von Werner, K. J. Fluorine Chem. 1985, 28, 229. (15) Ishihara, T.; Kuroboshi, M.; Okada, Y. Chem. Lett. 1986, 1895. (16) Urata, H.; Yugari, H.; Fuchikami, T. Chem. Lett. 1987, 833. (17) Hu, C.-M.; Qiu, Y.-L. J. Fluorine Chem. 1991, 55, 113. (18) Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648. (19) Hughes, R. P.; Lindner, D. C.; Smith, J. M.; Zhang, D.; Incarvito, C. D.; Lam, K.-C.; Liable-Sands, L. M.; Sommer, R. D.; Rheingold, A. L. J. Chem. Soc., Dalton Trans. 2001, 2270. (20) Bourgeois, C. J.; Huang, H.; Larichev, R. B.; Zakharov, L. N.; Rheingold, A. L.; Hughes, R. P. Organometallics 2007, 26, 264. (21) Hughes, R. P.; Lindner, D. C. J. Am. Chem. Soc. 1997, 119, 11544. (22) Hughes, R. P.; Lindner, D. C.; Rheingold, A. L.; Yap, G. P. A. Organometallics 1996, 15, 5678. (23) McCleverty, J. A.; Wilkinson, G. J. Chem. Soc. 1964, 4200. (24) Hughes, R. P.; Le Husebo, T. Organometallics 1997, 16, 5. (25) King, R. B.; Efraty, A. J. Organomet. Chem. 1972, 36, 371. (26) Gardner, S. A.; Rausch, M. D. Inorg. Chem. 1974, 13, 997. (27) Churchill, M. R. Inorg. Chem. 1965, 4, 1734. (28) Hughes, R. P.; Laritchev, R. B.; Williamson, A.; Incarvito, C. D.; Zakharov, L. N.; Rheingold, A. L. Organometallics 2002, 21, 4873. (29) Hughes, R. P.; Le Husebo, T.; Maddock, S. M.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 2002, 21, 243. (30) Hughes, R. P.; Le Husebo, T.; Holliday, B. J.; Rheingold, A. L.; Liable-Sands, L. M. J. Organomet. Chem. 1997, 548, 109. (31) Hughes, R. P.; Smith, J. M.; Liable-Sands, L. M.; Concolino, T. E.; Lam, K.-C.; Incarvito, C. D.; Rheingold, A. L. J. Chem. Soc., Dalton Trans. 2000, 873. (32) Bourgeois, C. J.; Hughes, R. P.; Husebo, T. L.; Smith, J. M.; Guzei, I. A.; Liable-Sands, L. M.; Zakharov, L. N.; Rheingold, A. L. Organometallics 2005, 24, 6431. Article (33) Yuan, J.; Hughes, R. P.; Rheingold, A. L. Organometallics 2011, 30, 1744. (34) Moseley, K.; Kang, J. W.; Maitlis, P. M. J. Chem. Soc. A 1970, 2875. (35) Werner, H.; Feser, R. J. Organomet. Chem. 1982, 232, 351. (36) King, R. B. Inorg. Chem. 1963, 2, 528. (37) Klingert, B.; Werner, H. Chem. Ber. 1983, 116, 1450. (38) Mukhedkar, A. J.; Mukhedkar, V. A.; Green, M.; Stone, F. G. A. J. Chem. Soc. A 1970, 3158. (39) Hughes, R. P.; Lindner, D. C.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 2001, 20, 363. (40) Oliver, A. J.; Graham, W. A. G. Inorg. Chem. 1971, 10, 1165. (41) Bowden, A. A.; Hughes, R. P.; Lindner, D. C.; Incarvito, C. D.; Liable-Sands, L. M.; Rheingold, A. L. J. Chem. Soc., Dalton Trans. 2002, 3245. (42) Hughes, R. P.; Maddock, S. M.; Guzei, I. A.; Liable-Sands, L. M.; Rheingold, A. L. J. Am. Chem. Soc. 2001, 123, 3279. (43) Hughes, R. P.; Maddock, S. M.; Rheingold, A. L.; Liable-Sands, L. M. J. Am. Chem. Soc. 1997, 119, 5988. (44) Kunicki, A. R.; Isobe, K.; Maitlis, P. M. J. Organomet. Chem. 1990, 399, 199. (45) Corkey, B. K.; Taw, F. L.; Bergman, R. G.; Brookhart, M. Polyhedron 2004, 23, 2943. (46) Monti, D.; Bassetti, M.; Sunley, G. J.; Ellis, P.; Maitlis, P. Organometallics 1991, 10, 4015. (47) Churchill, M. R.; Julis, S. A. Inorg. Chem. 1979, 18, 2918. (48) Churchill, M. R.; Julis, S. A. Inorg. Chem. 1979, 18, 1215. (49) Yuan, J.; Hughes, R. P.; Golen, J. A.; Rheingold, A. L. Organometallics 2010, 29, 1942. (50) Yuan, J.; Hughes, R. P.; Rheingold, A. L. Inorg. Chim. Acta 2010, 364, 96. (51) The chemical environment <strong>of</strong> the proton and fluorine nuclei should be very similar for both diastereomers because the stereogenic centers are far away from each other and separated from the metal by a 1,2-ethylene chain. (52) Hughes, R. P.; Kovacik, I.; Lindner, D. C.; Smith, J. M.; Willemsen, S.; Zhang, D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2001, 20, 3190. (53) Shenderovich, I. G.; Limbach, H.-H.; Smirnov, S. N.; Tolstoy, P. M.; Denisov, G. S.; Golubev, N. S. Phys. Chem. Chem. Phys. 2002, 4, 5488. (54) Christe, K. O.; Wilson, W. W. J. Fluorine Chem. 1990, 46, 339. (55) Brownstein, S. Can. J. Chem. 1980, 58, 1407. (56) Cambridge Structural Database search, version 5.32, Nov. 2010. (57) Kirsch, P. Modern Fluoroorganic Chemistry; Wiley-VCH: Weinheim, 2004. (58) Cabot, R.; Hunter, C. A. Chem. Commun. 2009, 2005. (59) Wakselman, C.; Lantz, A. In Organ<strong>of</strong>luorine Chemistry. Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; p 177. (60) Cavallotti, C.; Metrangolo, P.; Meyer, F.; Recupero, F.; Resnati, G. J. Phys. Chem. A 2008, 112, 9911. (61) Hughes, R. P.; Larichev, R. B.; Zakharov, L. N.; Rheingold, A. L. Organometallics 2005, 24, 4845. (62) Wakselman, C. J. Fluorine Chem. 1992, 59, 367. (63) Wu, F.; Xiao, F.; Yang, X.; Shen, Y.; Pan, T. Tetrahedron 2006, 62, 10091. (64) Feiring, A. E. J. Org. Chem. 1985, 50, 3269. (65) Toscano, P. J.; Barren, E. J. Chem. Soc., Chem. Commun. 1989, 1159. (66) Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255. (67) These reactions were performed with in situ generated complexes using a toluene solution <strong>of</strong> trimethylphosphine. If perfluoroalkyl radicals were generated, they could abstract H from toluene. (68) Diversi, P.; Ingrosso, G.; Lucherini, A.; Martinelli, P.; Benetti, M.; Pucci, S. J. Organomet. Chem. 1979, 165, 253. (69) Jones, W. D.; Feher, F. J. Inorg. Chem. 1984, 23, 2376. (70) Tedesco, V.; Philipsborn, W. Magn. Reson. Chem. 1996, 34, 373. 1298 dx.doi.org/10.1021/om2009588 | Organometallics 2012, 31, 1287−1299
Organometallics Article (71) Blancou, H.; Moreau, P.; Commeyras, A. Tetrahedron 1977, 33, 2061. (72) Foris, A. Magn. Reson. Chem. 2004, 42, 534. (73) Andreades, S. J. Am. Chem. Soc. 1964, 86, 2003. (74) Johnson, S. A.; Taylor, E. T.; Cruise, S. J. Organometallics 2009, 28, 3842. 1299 dx.doi.org/10.1021/om2009588 | Organometallics 2012, 31, 1287−1299
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