The trifluoromethyl group in transition metal chemistry

European Journal of Inorganic Chemistry

Volumn , Issue 31, 2012, Pages 4945-4966

  García Monforte, M Angeles ^a   Martínez Salvador, Sonia ^a   Menjõn, Babil ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

Fluorinated ligands; Fluorine; Transition metals

Indexed keywords

FLUORINE;

FLUORINATED LIGANDS; REACTIVITY PATTERN; STRUCTURAL FEATURE; TRANSITION METAL CHEMISTRY; TRIFLUOROMETHYL; TRIFLUOROMETHYL GROUP;

TRANSITION METALS;

EID: 84867777180     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201200620     Document Type: Review

References (253)

1. Fluorine is the 13th most abundant element in the Earth's crust with 585 ppm mean content (mass fraction):, P. Enghag, Encyclopedia of the Elements, Wiley-VCH, Weinheim, Germany, 2004, section 50.1, pp. 1073-1077.
2. -1 has been estimated for the C-F bond energy; this is the strongest bond formed by carbon with any chemical element (including itself):, J. E. Huheey, E. A. Kreiter, R. L. Kreiter, Inorganic Chemistry, 4th ed., Harper-Collins College Publishers, New York, 1993, Appendix E, pp. A21-A34.
3. Just a handful of fluorinated natural products are currently known, see:, D. O'Hagan, D. B. Harper, J. Fluorine Chem. 1999, 100, 127.
4. H. Schofield, J. Fluorine Chem. 1999, 100, 7.
5. D. O'Hagan, Chem. Soc. Rev. 2008, 37, 308.
6. B. E. Smart, J. Fluorine Chem. 2001, 109, 3.
7. J. A. Young, J. Chem. Educ. 1970, 47, 733. See also ref.[6]
8. 3 group shows a remarkable ability to stabilize highly strained organic molecules in general and different valence-bond isomers of aromatic and heteroaromatic compounds in particular: Y. Kobayashi, I. Kumadaki, Acc. Chem. Res. 1981, 14, 76 and references therein.
9. T. Okazoe, Proc. Jpn. Acad., Ser. B 2009, 85, 276.
10. K. Uneyama, Organofluorine Chemistry, Blackwell, Oxford, 2006.
11. J. Percy (Ed.), Science of Synthesis, vol. 34: Fluorine, Thieme, Stuttgart, Germany, 2005.
12. P. Kirsh, Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, Germany, 2004.
13. R. D. Chambers, Fluorine in Organic Chemistry, Blackwell Publishing Ltd, Oxford, UK, 2004.
14. D. M. Lemal, J. Org. Chem. 2004, 69, 1.
15. G. Sandford, Tetrahedron 2003, 59, 437.
16. T. Hiyama, Organofluorine Compounds: Chemistry and Applications (Ed.:, H. Yamamoto), Springer, Berlin, 2000.
17. G. Sandford, Philos. Trans. R. Soc. London Ser. A 2000, 358, 455.
18. B. Baasner, H. Hagemann, J. C. Tatlow, in: Methoden der organischen Chemie (Houben-Weyl), 4th ed., vol. E10: Organo-Fluorine Compounds, Thieme, Stuttgart, Germany, 1999.
19. R. E. Banks, J. C. Tatlow, J. Fluorine Chem. 1986, 33, 227.
20. J. E. Huheey, E. A. Kreiter, R. L. Kreiter, Inorganic Chemistry, 4th Ed. HarperCollins College Publishers, New York, 1993, pp. 182-199.
21. S. G. Bratsch, J. Chem. Educ. 1985, 62, 101.
22. T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470.
23. Frédéric Swarts (1866-1940) can be considered a true pioneer of organofluorine chemistry:, J. Timmermans, J. Chem. Educ. 1961, 38, 423.
24. J. Timmermans, J. Chem. Educ. 1961, 38, 423.
25. J. Timmermans, J. Chem. Soc. 1946, 559.
26. F. Swarts, Bull. Acad. Roy. Belgique 1898, 35, 375.
27. F. Swarts, Bull. Soc. Chim. Belg. 1923, 32, 102.
28. F. Swarts, Bull. Acad. Roy. Belgique, Cl. Sci. 1922, 8, 343.
29. R. N. Haszeldine, J. M. Kidd, J. Chem. Soc. 1954, 4228. See also:, R. D. Howells, J. D. McCown, Chem. Rev. 1977, 77, 69.
30. Biographic sketches of Harry J. Emeléus (1903-1993) are to be found in:, E. Banks, in: Fluorine Chemistry at the Millenium-Fascinated by Fluorine (Ed.:, E. Banks), Elsevier Science Ltd, Oxford, UK, 2000, pp. 62-63.
31. N. N. Greenwood, J. M. Shreeve, J. Fluorine Chem. 1999, 100, 15.
32. N. N. Greenwood, J. M. Shreeve, J. Fluorine Chem. 1999, 100, 15.
33. D. W. A. Sharp, Chem. Br. 1994, 30, 505.
34. 3COOI:, R. N. Haszeldine, J. Chem. Soc. 1951, 584.
35. J. Banus, H. J. Emeléus, R. N. Haszeldine, J. Chem. Soc. 1951, 60.
36. H. J. Emeléus, The Chemistry of Fluorine and Its Compounds, Academic Press, New York, 1969.
37. H. J. Emeléus, Angew. Chem. 1962, 74, 189; Angew. Chem. Int. Ed. Engl. 1962, 1, 129.
38. R. E. Banks, R. N. Haszeldine, Adv. Inorg. Chem. Radiochem. 1961, 3, 337.
39. H. J. Emeléus, Proc. Chem. Soc. 1960, 234.
40. J. J. Lagowski, Q. Rev. Chem. Soc. 1959, 13, 233.
41. H. J. Emeléus, J. Chem. Soc. 1954, 2979.
42. F. W. Bennett, H. J. Emeléus, R. N. Haszeldine, J. Chem. Soc. 1953, 1565.
43. 3:, O. Shyshkov, U. Dieckbreder, T. Drews, A. Kolomeitsev, G.-V. Röschenthaler, K. Seppelt, Inorg. Chem. 2009, 48, 6083.
44. H. J. Emeléus, R. N. Haszeldine, J. Chem. Soc. 1949, 2948.
45. H. J. Emeléus, R. N. Haszeldine, J. Chem. Soc. 1949, 2953.
46. T. H. Coffield, J. Kozikowski, R. D. Closson, in: International Conference on Coordination Chemistry, Chemical Society (Special Publication, No. 13), London, UK, 1959, p. 126.
47. H. D. Kaesz, R. B. King, F. G. A. Stone, Z. Naturforsch. B 1960, 15, 763.
48. W. R. McClellan, J. Am. Chem. Soc. 1961, 83, 1598.
49. F. G. A. Stone (1925-2011) has been one of the most prominent and prolific personalities in modern organometallic chemistry, see:, P. M. Maitlis, A. F. Hill, Organometallics 2012, 31, 2489.
50. P. M. Maitlis, A. F. Hill, Organometallics 2012, 31, 2489.
51. P. M. Maitlis, A. F. Hill, Organometallics 2012, 31, 2489.
52. P. M. Maitlis, A. F. Hill, Organometallics 2012, 31, 2489.
53. F. G. A. Stone, Leaving No Stone Unturned: Pathways in Organometallic Chemistry (Ed.:, L. I. Seeman), American Chemical Society, Washington DC, 1993.
54. R. P. Hughes, J. Fluorine Chem. 2010, 131, 1059.
55. R. P. Hughes, Eur. J. Inorg. Chem. 2009, 4591.
56. M. A. García-Monforte, P. J. Alonso, J. Forniés, B. Menjõn, Dalton Trans. 2007, 3347.
57. F. G. A. Stone, J. Fluorine Chem. 1999, 100, 227.
58. R. P. Hughes, Adv. Organomet. Chem. 1990, 31, 183.
59. R. Usõn, J. Forniés, Adv. Organomet. Chem. 1988, 28, 219.
60. F. G. A. Stone, Pure Appl. Chem. 1972, 30, 551.
61. R. Nyholm, Q. Rev. Chem. Soc. 1970, 24, 1.
62. F. G. A. Stone, Endeavour 1966, 25, 33.
63. P. M. Treichel, F. G. A. Stone, Adv. Organomet. Chem. 1964, 1, 143.
64. D. J. Burton, L. Lu, Top. Curr. Chem. 1997, 193, 45.
65. D. J. Burton, Z.-Y. Yang, P. A. Morken, Tetrahedron 1994, 50, 2993.
66. B. Beagley, G. G. Young, J. Mol. Struct. 1977, 40, 295.
67. F. A. Cotton, R. M. Wing, J. Organomet. Chem. 1967, 9, 511.
68. F. A. Cotton, R. M. Wing, J. Organomet. Chem. 1967, 9, 511.
69. R. B. King, M. B. Bisnette, J. Organomet. Chem. 1964, 2, 15.
70. [26]
71. On the importance of negative (anionic) hyperconjugation, sometimes referred to as "double bond-no bond resonance", see: P. v. Ragué Schleyer, A. J. Kos, Tetrahedron 1983, 39, 1141. cf. also:, W. B. Farnham, B. E. Smart, W. J. Middleton, J. C. Calabrese, D. A. Dixon, J. Am. Chem. Soc. 1985, 107, 4565.
72. J. D. Roberts, R. L. Webb, E. A. McElhill, J. Am. Chem. Soc. 1950, 72, 408.
73. 3 ligand has recently been assessed by theoretical calculations, which show that low-lying * C-F orbitals polarized toward the carbon atom are indeed able to overlap with the metal donor orbitals:, T. Leyssens, D. Peeters, A. G. Orpen, J. N. Harvey, Organometallics 2007, 26, 2637.
74. A. G. Algarra, V. V. Grushin, S. A. Macgregor, Organometallics 2012, 31, 1467.
75. J. Goodman, V. V. Grushin, R. B. Larichev, S. A. Macgregor, W. J. Marshall, D. C. Roe, J. Am. Chem. Soc. 2010, 132, 12013.
76. O. A. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475.
77. E. Pitcher, A. D. Buckingham, F. G. A. Stone, J. Chem. Phys. 1962, 36, 124.
78. For recent examples of decarbonylation of trifluoroacetyl-metal compounds, see:, B. D. Panthi, S. L. Gipson, A. Franken, Organometallics 2010, 29, 5890.
79. H. Huang, R. P. Hughes, A. L. Rheingold, Organometallics 2010, 29, 1948.
80. 2 in the presence of carbonate:, R. Eujen, Inorg. Synth. 1986, 24, 52.
81. - of all three Group 11 metals (M = Cu, Ag, Au) has been thoroughly studied in the gas phase by combined experimental (mass spectrometry) and theoretical (DFT) methods:, N. J. Rijs, R. A. J. O'Hair, Dalton Trans. 2012, 41, 3395. Evidence for difluorocarbene extrusion has also been obtained.
82. 6 vapors:, R. J. Lagow, J. A. Morrison, Adv. Inorg. Chem. Radiochem. 1980, 23, 177.
83. J. A. Morrison, Adv. Organomet. Chem. 1993, 35, 211.
84. M. Finze, E. Bernhardt, H. Willner, Angew. Chem. 2007, 119, 9340; Angew. Chem. Int. Ed. 2007, 46, 9180.
85. 3
86. E. Bernhardt, M. Finze, H. Willner, Inorg. Chem. 2011, 50, 10268.
87. S. Balters, E. Bernhardt, H. Willner, T. Berends, Z. Anorg. Allg. Chem. 2004, 630, 257 see also
88. S. Balters, Ph. D. Thesis, University of Wuppertal, 2005 [urn:nbn:de:hbz:468-20050702].
89. E. Bernhardt, M. Finze, H. Willner, J. Fluorine Chem. 2004, 125, 967.
90. G. K. S. Prakash, M. Mandal, J. Fluorine Chem. 2001, 112, 123.
91. G. K. S. Prakash, A. K. Yudin, Chem. Rev. 1997, 97, 757.
92. D. Naumann, N. V. Kirij, N. Maggiarosa, W. Tyrra, Y. L. Yagupolskii, M. S. Wickleder, Z. Anorg. Allg. Chem. 2004, 630, 746.
93. N. Maggiarosa, W. Tyrra, D. Naumann, N. V. Kirij, Y. L. Yagupolskii, Angew. Chem. 1999, 111, 2392; Angew. Chem. Int. Ed. 1999, 38, 2252.
94. J. Vicente, J. Gil-Rubio, J. Guerrero-Leal, D. Bautista, Organometallics 2004, 23, 4871.
95. J. Vicente, J. Gil-Rubio, J. Guerrero-Leal, D. Bautista, Dalton Trans. 2009, 3854.
96. Note that the use of excellent donor Cp ligands helps to mitigate the metal-center acidity. Even so, these compounds are shock-sensitive in the solid state and susceptible to violent decomposition, probably as the result of fluoride migration from C to Ti (1,2-shift), see:, F. L. Taw, A. E. Clark, A. H. Mueller, M. T. Janicke, T. Cantat, B. L. Scott, P. J. Hay, R. P. Hughes, J. L. Kiplinger, Organometallics 2012, 31, 1484.
97. F. L. Taw, B. L. Scott, J. L. Kiplinger, J. Am. Chem. Soc. 2003, 125, 14712.
98. S. K. Ritter, Chem. Eng. News 2012, 90, 10.
99. S. K. Ritter, Chem. Eng. News 2012, 90, 10.
100. S. K. Ritter, Chem. Eng. News 2012, 90, 10.
101. W. R. Dolbier Jr., J. Fluorine Chem. 2005, 126, 157, and references cited therein.
102. A. Studer, Angew. Chem. 2012, 124, 9082; Angew. Chem. Int. Ed. 2012, 51, 8950
103. X.-F. Wu, H. Neumann, M. Beller, Chem. Asian J. 2012, 7, 1744.
104. J. Nie, H.-C. Guo, D. Cahard, J.-A. Ma, Chem. Rev. 2011, 111, 455.
105. S. Roy, B. T. Gregg, G. W. Gribble, V.-D. Le, S. Roy, Tetrahedron 2011, 67, 2161.
106. D. A. Nagib, D. W. C. MacMillan, Nature 2011, 480, 224.
107. E. Lele, S. Qilong, L. Long, Chimia 2011, 65, 894.
108. J.-A. Ma, D. Cahard, Chem. Rev. 2008, 108, PR1.
109. J.-A. Ma, D. Cahard, Chem. Rev. 2008, 108, PR1.
110. J.-A. Ma, D. Cahard, J. Fluorine Chem. 2007, 128, 975.
111. T. Billard, B. R. Langlois, Eur. J. Org. Chem. 2007, 891.
112. B. R. Langlois, T. Billard, S. Roussel, J. Fluorine Chem. 2005, 126, 173.
113. P. R. Singh, J. M. Shreeve, Tetrahedron 2000, 56, 7613.
114. T. G. Richmond, Angew. Chem. 2000, 112, 3378; Angew. Chem. Int. Ed. 2000, 39, 3241.
115. [9,33]
116. G. G. Dubinina, H. Furutachi, D. A. Vicic, J. Am. Chem. Soc. 2008, 130, 8600.
117. G. G. Dubinina, J. Ogikubo, D. A. Vicic, Organometallics 2008, 27, 6233.
118. M. Oishi, H. Kondo, H. Amii, Chem. Commun. 2009, 1909.
119. H. Morimoto, T. Tsubogo, N. D. Litvinas, J. F. Hartwig, Angew. Chem. 2011, 123, 3877; Angew. Chem. Int. Ed. 2011, 50, 3793.
120. N. D. Litvinas, P. S. Fier, J. F. Hartwing, Angew. Chem. 2012, 124, 551; Angew. Chem. Int. Ed. 2012, 51, 536.
121. L. L. Chu, F.-L. Qing, J. Am. Chem. Soc. 2010, 132, 7262.
122. L. L. Chu, F.-L. Qing, Org. Lett. 2010, 12, 5060.
123. T. D. Senecal, A. T. Parsons, S. L. Buchwald, J. Org. Chem. 2011, 76, 1174.
124. X. L. Jiang, L. L. Chu, F.-L. Qing, J. Org. Chem. 2012, 77, 1251.
125. Z. Q. Weng, R. Lee, W. G. Jia, Y. F. Yuan, W. F. Wang, X. Feng, K.-W. Huang, Organometallics 2011, 30, 3229.
126. Y. Usui, J. Noma, M. Hirano, S. Komiya, Inorg. Chim. Acta 2000, 309, 151.
127. O. A. Tomashenko, E. C. Escudero-Adán, M. M. Belmonte, V. V. Grushin, Angew. Chem. 2011, 123, 7797; Angew. Chem. Int. Ed. 2011, 50, 7655.
128. M. A. Willert-Porada, D. J. Burton, N. C. Baenziger, J. Chem. Soc., Chem. Commun. 1989, 1633.
129. E. J. Cho, S. L. Buchwald, Org. Lett. 2011, 13, 6552.
130. E. J. Cho, T. D. Senecal, T. Kinzel, Y. Zhang, D. A. Watson, S. L. Buchwald, Science 2010, 328, 1679.
131. [9,33,50d] and references therein.
132. D. A. Culkin, J. F. Hartwig, Organometallics 2004, 23, 3398.
133. V. V. Grushin, W. J. Marshall, J. Am. Chem. Soc. 2006, 128, 12644.
134. V. I. Bakhmutov, F. Bozoglian, K. Gõmez, G. González, V. V. Grushin, S. A. Macgregor, E. Martín, F. M. Miloserdov, M. A. Novikov, J. A. Panetier, L. V. Romashov, Organometallics 2012, 31, 1315.
135. V. V. Grushin, W. J. Marshall, J. Am. Chem. Soc. 2006, 128, 4632.
136. P. Anstaett, F. Schoenebeck, Chem. Eur. J. 2011, 17, 12340.
137. N. D. Ball, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 2010, 132, 2878.
138. N. D. Ball, J. B. Gary, Y. D. Ye, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 7577.
139. Y. D. Ye, N. D. Ball, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 2010, 132, 14682.
140. D. C. Powers, E. Lee, A. Ariafard, M. S. Sanford, B. F. Yates, A. J. Canty, T. Ritter, J. Am. Chem. Soc. 2012, 134, 12002.
141. J. Forniés, A. Martín, in: Metal Clusters in Chemistry, vol. 1, Molecular Metal Clusters (Eds.:, P. Braunstein, L. A. Oro, P. R. Raithby), Wiley-VCH, Weinheim, Germany, 1999, pp. 417-443.
142. S. Komiya, Y. Abe, A. Yamamoto, T. Yamamoto, Organometallics 1983, 2, 1466.
143. G. G. Dubinina, W. W. Brennessel, J. L. Miller, D. A. Vicic, Organometallics 2008, 27, 3933.
144. D. J. Brauer, H. Burger, R. Eujen, J. Organomet. Chem. 1977, 135, 281.
145. A. J. Downs, J. Chem. Soc. 1963, 5273.
146. R. J. Lagow, R. Eujen, L. L. Gerchman, J. A. Morrison, J. Am. Chem. Soc. 1978, 100, 1722.
147. J. A. Morrison, L. L. Gerchman, R. Eujen, R. J. Lagow, J. Fluorine Chem. 1977, 10, 333.
148. E. A. Ganja, C. D. Ontiveros, J. A. Morrison, Inorg. Chem. 1988, 27, 4535.
149. B. L. Dyatkin, B. I. Martynov, I. L. Knunyants, S. R. Sterlin, L. A. Fedorof, Z. A. Stumbrevichute, Tetrahedron Lett. 1971, 12, 1345.
150. L. J. Krause, J. A. Morrison, J. Am. Chem. Soc. 1981, 103, 2995.
151. H. Lange, D. Naumann, J. Fluorine Chem. 1984, 26, 1.
152. M. A. Guerra, T. R. Bierschenk, R. J. Lagow, J. Am. Chem. Soc. 1986, 108, 4103.
153. D. C. Loizou, J. Castillo, A. R. Oki, N. S. Hosmane, J. A. Morrison, Organometallics 1992, 11, 4189.
154. W. Dukat, D. Naumann, J. Chem. Soc., Dalton Trans. 1989, 739.
155. C. D. Ontiveros, J. A. Morrison, Organometallics 1986, 5, 1446.
156. L. J. Krause, J. A. Morrison, J. Chem. Soc., Chem. Commun. 1981, 1282.
157. H. H. Murray, J. P. Fackler Jr, L. C. Porter, D. A. Briggs, M. A. Guerra, R. J. Lagow, Inorg. Chem. 1987, 26, 357.
158. R. D. Sanner, J. H. Satcher Jr, M. W. Droege, Organometallics 1989, 8, 1498.
159. H. K. Nair, J. A. Morrison, J. Organomet. Chem. 1989, 376, 149.
160. W. Dukat, D. Naumann, Rev. Chim. Min. 1986, 23, 589.
161. D. Nauman, W. Tyrra, J. Organomet. Chem. 1989, 368, 131.
162. D. Naumann, W. Strauß, W. Tyrra, J. Organomet. Chem. 1991, 407, 1.
163. M. A. Guerra, S. K. Mehrotra, D. W. Dyer, R. J. Lagow, J. Organomet. Chem. 1990, 390, C73.
164. H. K. Nair, J. A. Morrison, Inorg. Chem. 1989, 28, 2816.
165. L. J. Krause, J. A. Morrison, J. Chem. Soc., Chem. Commun. 1980, 671.
166. H. Lange, D. Naumann, J. Fluorine Chem. 1985, 27, 309.
167. J. K. Galiotos, J. A. Morrison, Organometallics 2000, 19, 2603.
168. D. Naumann, W. Tyrra, F. Leifeld, J. Organomet. Chem. 1987, 333, 193.
169. D. Naumann, W. Tyrra, J. Organomet. Chem. 1987, 334, 323.
170. D. Naumann, B. Wilkes, J. Fluorine Chem. 1985, 27, 115.
171. W. Tyrra, D. Naumann, Can. J. Chem. 1991, 69, 327.
172. E. K. S. Liu, L. B. Asprey, J. Organomet. Chem. 1979, 169, 249.
173. J. Behm, S. D. Lotz, W. A. Herrmann, Z. Anorg. Allg. Chem. 1993, 619, 849.
174. E. K. S. Liu, Inorg. Chem. 1980, 19, 266.
175. H. Lange, D. Naumann, J. Fluorine Chem. 1984, 26, 435.
176. D. Naumann, W. Tyrra, B. Kock, W. Rudolph, B. Wilkes, J. Fluorine Chem. 1994, 67, 91.
177. D. J. Burton, D. M. Wiemers, J. Am. Chem. Soc. 1985, 107, 5014.
178. K. J. Klabunde, M. S. Key, J. Y. F. Low, J. Am. Chem. Soc. 1972, 94, 999.
179. D. M. Wiemers, D. J. Burton, J. Am. Chem. Soc. 1986, 108, 832.
180. P. J. Brothers, W. R. Roper, Chem. Rev. 1988, 88, 1293.
181. M. Klahn, U. Rosenthal, Organometallics 2012, 31, 1235.
182. M. Klahn, U. Rosenthal, Organometallics 2012, 31, 1235.
183. M. Klahn, U. Rosenthal, Organometallics 2012, 31, 1235.
184. J. L. Kiplinger, T. G. Richmond, C. E. Osterberg, Chem. Rev. 1994, 94, 373.
185. D. L. Reger, M. D. Dukes, J. Organomet. Chem. 1978, 153, 67.
186. T. G. Richmond, A. M. Crespi, D. F. Shriver, Organometallics 1984, 3, 314.
187. J. D. Koola, D. M. Roddick, Organometallics 1991, 10, 591.
188. T. G. Richmond, D. F. Shriver, Organometallics 1984, 3, 305.
189. T. G. Richmond, D. F. Shriver, Organometallics 1983, 2, 1061.
190. A. M. Crespi, D. F. Shriver, Organometallics 1985, 4, 1830.
191. S. Anderson, A. F. Hill, G. R. Clark, Organometallics 1992, 11, 1988.
192. G. R. Clark, S. V. Hoskins, T. C. Jones, W. R. Roper, J. Chem. Soc., Chem. Commun. 1983, 719.
193. W. R. Roper, J. Organomet. Chem. 1986, 300, 167.
194. M. A. Gallop, W. R. Roper, Adv. Organomet. Chem. 1986, 25, 121.
195. G. R. Clark, S. V. Hoskins, W. R. Roper, J. Organomet. Chem. 1982, 234, C9.
196. D. J. Huang, P. R. Koren, K. Folting, E. R. Davidson, K. G. Caulton, J. Am. Chem. Soc. 2000, 122, 8916.
197. D. J. Huang, K. G. Caulton, J. Am. Chem. Soc. 1997, 119, 3185.
198. P. J. Brothers, A. K. Burrell, G. R. Clark, C. E. F. Rickard, W. R. Roper, J. Organomet. Chem. 1990, 394, 615.
199. R. P. Hughes, R. B. Laritchev, J. Yuan, J. A. Golen, A. N. Rucker, A. L. Rheingold, J. Am. Chem. Soc. 2005, 127, 15020.
200. C. J. Bourgeois, R. P. Hughes, J. Yuan, A. G. DiPasquale, A. L. Rheingold, Organometallics 2006, 25, 2908.
201. A. K. Burrell, G. R. Clark, J. G. Jeffrey, C. E. F. Rickard, W. R. Roper, J. Organomet. Chem. 1990, 388, 391.
202. P. J. Albietz, J. F. Houlis, R. Eisenbenrg, Inorg. Chem. 2002, 41, 2001.
203. R. A. Michelin, R. Ros, G. Guadalupi, G. Bombieri, F. Benetollo, G. Chapuis, Inorg. Chem. 1989, 28, 840.
204. P. Sgarbossa, A. Scarso, G. Strukul, R. A. Michelin, Organometallics 2012, 31, 1257.
205. U. Belluco, R. A. Michelin, R. Ros, R. Bertani, G. Facchin, M. Mozzon, L. Zanotto, Inorg. Chim. Acta 1992, 198-200, 883.
206. R. A. Michelin, G. Facchin, R. Ros, J. Organomet. Chem. 1985, 279, C25.
207. T. G. Appleton, R. D. Berry, J. R. Hall, D. W. Neale, J. Organomet. Chem. 1989, 364, 249.
208. S. Martínez-Salvador, B. Menjõn, J. Forniés, A. Martín, I. Usõn, Angew. Chem. 2010, 122, 4382; Angew. Chem. Int. Ed. 2010, 49, 4286.
209. A. Haaland, Angew. Chem. 1989, 101, 1017; Angew. Chem. Int. Ed. Engl. 1989, 28, 992.
210. Z.-Y. Yang, D. M. Wiemers, D. J. Burton, J. Am. Chem. Soc. 1992, 114, 4402.
211. D. Zopes, S. Kremer, H. Seherer, L. Belkoura, I. Pantenburg, W. Tyrra, S. Mathur, Eur. J. Inorg. Chem. 2011, 273.
212. S. Martínez-Salvador, J. Forniés, A. Martín, B. Menjõn, Angew. Chem. 2011, 123, 6701; Angew. Chem. Int. Ed. 2011, 50, 6571.
213. D. B. dell'Amico, F. Calderazzo, P. Robino, A. Segre, J. Chem. Soc., Dalton Trans. 1991, 3017.
214. J. Browning, P. L. Goggin, R. J. Goodfellow, M. G. Norton, A. J. M. Rattray, B. F. Taylor, J. Mink, J. Chem. Soc., Dalton Trans. 1977, 2061.
215. C. J. Evans, L. M. Reynard, M. C. L. Gerry, Inorg. Chem. 2001, 40, 6123.
216. D. L. S. Brahms, W. P. Dailey, Chem. Rev. 1996, 96, 1585.
217. D. Seyferth, S. P. Hopper, J. Organomet. Chem. 1971, 26, C62.
218. I. L. Knunyants, Y. F. Komissarov, B. L. Dyatkin, L. T. Lantseva, Russ. Chem. Bull. 1973, 22, 912.
219. D. Naumann, F. Schulz, I. Pantenburg, W. Tyrra, Z. Anorg. Allg. Chem. 2004, 630, 529.
220. R. Eujen, B. Hoge, J. Organomet. Chem. 1995, 503, C51.
221. R. Eujen, R. Haiges, Z. Naturforsch. B 1998, 53, 1455.
222. D. Naumann, R. Möckel, W. Tyrra, Angew. Chem. 1994, 106, 325; Angew. Chem. Int. Ed. Engl. 1994, 33, 323.
223. J. Vicente, J. Gil-Rubio, J. Guerrero-Leal, D. Bautista, Organometallics 2005, 24, 5634.
224. T. G. Appleton, R. D. Berry, J. R. Hall, D. W. Neale, J. Organomet. Chem. 1988, 342, 399.
225. B. Menjõn, S. Martínez-Salvador, M. A. Gõmez-Saso, J. Forniés, L. R. Falvello, A. Martín, A. Tsipis, Chem. Eur. J. 2009, 15, 6371.
226. S. Martínez-Salvador, P. J. Alonso, J. Forniés, A. Martín, B. Menjõn, Dalton Trans. 2011, 40, 10440.
227. T. G. Appleton, J. R. Hall, D. W. Neale, M. A. Williams, J. Organomet. Chem. 1984, 276, C73.
228. S. Martínez-Salvador, J. Forniés, A. Martín, B. Menjõn, Chem. Eur. J. 2011, 17, 8085.
229. C. M. Mitchell, F. G. A. Stone, J. Chem. Soc. C 1970, 1263.
230. A. Johnson, R. J. Puddephatt, J. Chem. Soc., Dalton Trans. 1976, 1360.
231. J. L. Margrave, K. H. Whitmire, R. H. Hauge, N. T. Norem, Inorg. Chem. 1990, 29, 3252.
232. For recent advances on organocopper(III)chemistry, see:, A. J. Hickman, M. S. Sanford, Nature 2012, 484, 177.
233. D. Naumann, T. Roy, K.-F. Tebbe, W. Crump, Angew. Chem. 1993, 105, 1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1482.
234. G. Aullõn, S. Alvarez, Theor. Chem. Acc. 2009, 123, 67.
235. G. Aullõn, S. Alvarez, Theor. Chem. Acc. 2009, 123, 67.
236. G. Aullõn, S. Alvarez, Theor. Chem. Acc. 2009, 123, 67.
237. M. Kaupp, H. G. von Schnering, Angew. Chem. 1995, 107, 1076; Angew. Chem. Int. Ed. Engl. 1995, 34, 986.
238. J. A. Schlueter, J. M. Williams, U. Geiser, J. D. Dudek, S. A. Sirchio, M. E. Kelly, J. S. Gregar, W.-K. Kwok, J. A. Fendrich, J. E. Schirber, W. R. Bayless, D. Naumann, T. Roy, J. Chem. Soc., Chem. Commun. 1995, 1311.
239. S. Martínez-Salvador, L. R. Falvello, J. Forniés, A. Martín, B. Menjõn, manuscript in preparation.
240. U. Preiss, I. Krossing, Z. Anorg. Allg. Chem. 2007, 633, 1639.
241. J. A. Schlueter, U. Geiser, A. M. Kini, H. H. Wang, J. M. Williams, D. Naumann, T. Roy, B. Hoge, R. Eujen, Coord. Chem. Rev. 1999, 190-192, 781, and references cited therein.
242. E. Bernhardt, M. Berkei, H. Willner, Z. Anorg. Allg. Chem. 2009, 635, 2009.
243. E. Bernhardt, M. Berkei, H. Willner, Z. Anorg. Allg. Chem. 2009, 635, 2009.
244. E. Bernhardt, M. Berkei, H. Willner, Z. Anorg. Allg. Chem. 2009, 635, 2009.
245. E. Bernhardt, M. Berkei, H. Willner, Z. Anorg. Allg. Chem. 2009, 635, 2009.
246. M. Finze, E. Bernhardt, M. Berkei, H. Willner, J. Hung, R. M. Waymouth, Organometallics 2005, 24, 5103.
247. D. Naumann, W. Tyrra, F. Trinius, W. Wessel, T. Roy, J. Fluorine Chem. 2000, 101, 131.
248. R. Eujen, B. Hoge, D. J. Brauer, Inorg. Chem. 1997, 36, 1464.
249. S. Mathur, W. Tyrra, C. Hegemann, D. Zopes, Chem. Commun. 2012, 48, 8805.
250. 2) was obtained from its decomposition products:, E. L. Werkema, E. Messines, L. Perrin, L. Maron, O. Eisenstein, R. A. Andersen, J. Am. Chem. Soc. 2005, 127, 7781.
251. M. Finze, E. Bernhardt, M. Zähres, H. Willner, Inorg. Chem. 2004, 43, 490.
252. H. Huang, R. P. Hughes, A. L. Rheingold, Dalton Trans. 2011, 40, 47.
253. H. Huang, R. P. Hughes, C. R. Landis, A. L. Rheingold, J. Am. Chem. Soc. 2006, 128, 7454.