Fluorine as a ligand substituent in organometallic chemistry: A second chance and a second research career

Journal of Fluorine Chemistry

Volumn 131, Issue 11, 2010, Pages 1059-1070

  Hughes, Russell P ^a  

^a DARTMOUTH COLLEGE   (United States)

Author keywords

Fluorine; Organometallic; Transition metal

Indexed keywords

EID: 78049457751     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2010.06.014     Document Type: Article

References (136)

1. A history of fluorine chemistry at Manchester is provided R.E. Banks, Fluorine Chemistry at the Millennium. Fascinated by Fluorine 2000 Elsevier Amsterdam
2. A Reminiscences about organometallic fluorine chemistry in the early years in Bristol are included F.G.A. Stone, Leaving No Stone Unturned; Pathways in Organometallic Chemistry 1993 American Chemical Society
3. T.H. Coffield, J. Kozikowski, and R.D. Closson J. Org. Chem. 22 1957 598
4. R.D. Closson, J. Kozikowski, and T.H. Coffield J. Org. Chem. 22 1957 598
5. T.H. Coffield, J. Kozikowski, and R.D. Closson Abstr. I.C.C.C. Conference, vol. Special Publication No. 13 1959 The Chemical Society London 126
6. H.D. Kaesz, R.B. King, and F.G.A. Stone Z. Naturforsch. 15b 1960 763 764
7. W.R. McClellan J. Am. Chem. Soc. 83 1961 1598 1600
8. W. Hieber, W. Beck, and E. Lindner Z. Naturforsch. B 16b 1961 229 231
9. R.B. King, P.M. Treichel, and F.G.A. Stone Proc. Chem. Soc. 1961 69 70
10. T.A. Manuel, S.L. Stafford, and F.G.A. Stone J. Am. Chem. Soc. 83 1961 249 250
11. H.H. Hoehn, L. Pratt, K.F. Watterson, and G. Wilkinson J. Chem. Soc. 1961 2738 2745
12. G.W. Parshall, and G. Wilkinson J. Chem. Soc. 1962 1132
13. J.P. Collman Acc. Chem. Res. 1 1968 136 143
14. G.W. Parshall, and S.D. Ittel Homogeneous catalysis The Applications and Chemistry of Catalysis by Soluble Transition Metal Complexes second ed. 1992 Wiley-Interscience New York p. 342
15. D. Peters J. Chem. Phys. 38 1963 561 563
16. P. Hohenberg, and W. Kohn Phys. Rev. 136 1964 B864 B871
17. W. Kohn, and L.J. Sham Phys. Rev. 140 1965 A1133 A1138
18. D.M. Lemal, J.M. Buzby, A.C. Barefoot III, M.W. Grayston, and E.D. Laganis J. Org. Chem. 45 1980 3118 3120
19. M.G. Barlow, M.W. Crawley, and R.N. Haszeldine J. Chem. Soc. Perkin Trans. 1 1980 122 125
20. B.B. Laird, and R.E. Davis Acta Crystallogr. Sect. B 38 1982 678 680
21. R.P. Hughes Adv. Organomet. Chem. 31 1990 183 267
22. R. Willstaetter, and E. Waser Ber. Dtsch. Chem. Ges. 44 1911 3423 3445
23. T.A. Manuel, and F.G.A. Stone Proc. Chem. Soc. 1959 90
24. A. Nakamura, and N. Hagihara Bull. Chem. Soc. Jpn. 32 1959 880 881
25. A.C. Barefoot III, E.W. Corcoran Jr., R.P. Hughes, D.M. Lemal, W.D. Saunders, B.B. Laird, and R.E. Davis J. Am. Chem. Soc. 103 1981 970 972
26. R.P. Hughes, Unpublished observations.
27. T.A. Manuel, and F.G.A. Stone J. Am. Chem. Soc. 82 1960 366 372
28. R.T. Carl, R.P. Hughes, J.A. Johnson, R.E. Davis, and R.P. Kashyap J. Am. Chem. Soc. 109 1987 6875 6876
29. M.A. Bennett, and J.D. Saxby Inorg. Chem. 7 1968 321 324
30. R.P. Hughes, D.E. Samkoff, R.E. Davis, and B.B. Laird Organometallics 2 1983 195 197
31. R.P. Hughes, R.T. Carl, R.C. Hemond, D.E. Samkoff, and A.L. Rheingold J. Chem. Soc. Chem. Commun. 1986 306 308
32. R.T. Carl, S.J. Doig, W.E. Geiger, R.C. Hemond, R.P. Hughes, R.S. Kelly, and D.E. Samkoff Organometallics 6 1987 611 616
33. R.T. Carl, R.P. Hughes, and D.E. Samkoff Organometallics 7 1988 1625 1631
34. R.T. Carl, E.W. Corcoran Jr., R.P. Hughes, and D.E. Samkoff Organometallics 9 1990 838 844
35. P.L. Pauson, and J.A. Segal J. Chem. Soc., Dalton Trans. 1975 2387 2392
36. R.C. Hemond, R.P. Hughes, and A.L. Rheingold Organometallics 8 1989 1261 1269
37. G. Paprott, D. Lentz, and K. Seppelt Chem. Ber. 117 1984 1153 1160
38. G. Paprott, and K. Seppelt J. Am. Chem. Soc. 106 1984 4060 4061
39. G. Paprott, S. Lehmann, and K. Seppelt Chem. Ber. 121 1988 727 733
40. R.R. Soelch, G.W. Mauer, and D.M. Lemal J. Org. Chem. 50 1985 5845 5852
41. P.J. Fagan, M.D. Ward, and J.C. Calabrese J. Am. Chem. Soc. 111 1989 1698 1719
42. P.J. Fagan, W.S. Mahoney, J.C. Calabrese, and I.D. Williams Organometallics 9 1990 1843 1852
43. S.P. Nolan, K.L. Martin, D. Buzatu, M.L. Trudell, E.D. Stevens, and P.J. Fagan Struct. Chem. 4 1993 367 375
44. S.D. Loren, B.K. Campion, R.H. Heyn, T.D. Tilley, B.E. Bursten, and K.W. Luth J. Am. Chem. Soc. 111 1989 4712 4718
45. U. Koelle, M.H. Wang, and G. Raabe Organometallics 10 1991 2573 2577
46. Accessed http://en.wikipedia.org/wiki/Up-to-eleven May 15, 2010
47. O.J. Curnow, and R.P. Hughes J. Am. Chem. Soc. 114 1992 5895 5897
48. B.F. Johnston, D.W.H. Rankin, H.E. Robertson, R.P. Hughes, and J.R. Lomprey Organometallics 21 2002 4840 4846
49. R.P. Hughes, X. Zheng, R.L. Ostrander, and A.L. Rheingold Organometallics 13 1994 1567 1568
50. R.P. Hughes, X. Zheng, C.A. Morse, O.J. Curnow, J.R. Lomprey, A.L. Rheingold, and G.P.A. Yap Organometallics 17 1998 457 465
51. D.L. Lichtenberger, Y. Elkadi, N.E. Gruhn, R.P. Hughes, O.J. Curnow, and X. Zheng Organometallics 16 1997 5209 5217
52. D.E. Richardson, M.F. Ryan, W.E. Geiger, T.T. Chin, R.P. Hughes, and O.J. Curnow Organometallics 12 1993 613 615
53. D.E. Richardson, L. Lang, J.R. Eyler, S.R. Kircus, X. Zheng, C.A. Morse, and R.P. Hughes Organometallics 16 1997 149 150
54. B.E. Smart S. Patai, Z. Rappoport, Chemistry of Functional Groups, Supplement D vol. 1 1983 Wiley New York 603 655
55. B.E. Smart Mol. Struct. Eng. 3 1986 141 191
56. B.E. Smart M. Hudlicky, A. Pavlath, Chemistry of Organofluorine Compounds II 1995 American Chemical Society Washington D.C.
57. H.A. Bent Chem. Rev. 61 1961 275 311
58. H. Reihlen, A. Gruhl, G.v. Hessling, and O. Pfrengle Liebigs Ann. Chem. 482 1930 161 182
59. B.F. Hallam, and P.L. Pauson J. Chem. Soc. 1958 642 645
60. R.L. Hunt, D.M. Roundhill, and G. Wilkinson J. Chem. Soc. A 1967 982 984
61. P.B. Hitchcock, and R. Mason Chem. Commun. 1967 242 243
62. R.P. Hughes, P.R. Rose, X. Zheng, and A.L. Rheingold Organometallics 14 1995 2407 2414
63. O.J. Curnow, R.P. Hughes, and A.L. Rheingold J. Am. Chem. Soc. 114 1992 3153 3155
64. O.J. Curnow, R.P. Hughes, E.N. Mairs, and A.L. Rheingold Organometallics 12 1993 3102 3108
65. S.D. Ittel, and J.A. Ibers Adv. Organomet. Chem. 14 1976 33 61
66. L.J. Guggenberger, and R. Cramer J. Am. Chem. Soc. 94 1972 3779 3786
67. T.A. Albright, R. Hoffmann, J.C. Thibeault, and D.L. Thorn J. Am. Chem. Soc. 101 1979 3801 3812
68. D.M. Roundhill, D.N. Lawson, and G. Wilkinson J. Chem. Soc. A 1968 845 849
69. R.P. Hughes, P.R. Rose, and A.L. Rheingold Organometallics 12 1993 3109 3117
70. T.G. Richmond, A.M. Crespi, and D.F. Shriver Organometallics 3 1984 314 319
71. D.L. Reger, and M.D. Dukes J. Organomet. Chem. 153 1978 67 72
72. J.D. Koola, and D.M. Roddick Organometallics 10 1991 591 597
73. G.R. Clark, S.V. Hoskins, and W.R. Roper J. Organomet. Chem. 234 1982 C9 C12
74. T.G. Appleton, R.D. Berry, J.R. Hall, and D.W. Neale J. Organomet. Chem. 364 1989 249 273
75. A.K. Burrell, G.R. Clark, C.E.F. Rickard, and W.R. Roper J. Organomet. Chem. 482 1994 261 269
76. R.A. Michelin, G. Facchin, and R. Ros J. Organomet. Chem. 279 1985 C25 C28
77. R.A. Michelin, R. Ros, G. Guadalupi, G. Bombieri, F. Benetollo, and G. Chapuis Inorg. Chem. 28 1989 840 846
78. R.P. Hughes, D.C. Lindner, A.L. Rheingold, and L.M. Liable-Sands J. Am. Chem. Soc. 119 1997 11544 11545
79. R.P. Hughes, D.C. Lindner, J.M. Smith, D. Zhang, C.D. Incarvito, K.-C. Lam, L.M. Liable-Sands, R.D. Sommer, and A.L. Rheingold J. Chem. Soc., Dalton Trans. 2001 2270 2278
80. R.P. Hughes Eur. J. Inorg. Chem. 31 2009 4591 4606
81. R.P. Hughes, and J.M. Smith J. Am. Chem. Soc. 121 1999 6084 6085
82. R.P. Hughes, S. Willemsen, A. Williamson, and D. Zhang Organometallics 21 2002 3085 3087
83. S.A. Garratt, R.P. Hughes, I. Kovacik, A.J. Ward, S. Willemsen, and D. Zhang J. Am. Chem. Soc. 127 2005 15585 15594
84. R.P. Hughes, D. Zhang, L.N. Zakharov, and A.L. Rheingold Organometallics 21 2002 4902 4904
85. C.J. Bourgeois, Hughes, R.P., Unpublished observations.
86. R.P. Hughes, R.B. Laritchev, L.N. Zakharov, and A.L. Rheingold J. Am. Chem. Soc. 127 2005 6325 6334
87. R.P. Hughes, R.B. Larichev, L.N. Zakharov, and A.L. Rheingold Organometallics 25 2006 3943 3947
88. R.P. Hughes, R.B. Laritchev, J. Yuan, J.A. Golen, A.N. Rucker, and A.L. Rheingold J. Am. Chem. Soc. 127 2005 15020 15021
89. C.J. Bourgeois, R.P. Hughes, J. Yuan, A.G. DiPasquale, and A.L. Rheingold Organometallics 25 2006 2908 2910
90. J. Yuan, R.P. Hughes, and A.L. Rheingold Eur. J. Inorg. Chem. 2007 4723 4725
91. G.R. Clark, S.V. Hoskins, T.C. Jones, and W.R. Roper J. Chem. Soc., Chem. Commun. 1983 719 721
92. T.G. Richmond, and D.F. Shriver Organometallics 3 1984 305 314
93. A.M. Crespi, and D.F. Shriver Organometallics 4 1985 1830 1835
94. P.J. Brothers, and W.R. Roper Chem. Rev. 88 1988 1293 1326
95. P.J. Brothers, A.K. Burrell, G.R. Clark, C.E.F. Rickard, and W.R. Roper J. Organomet. Chem. 394 1990 615 642
96. D. Huang, P.R. Koren, K. Folting, E.R. Davidson, and K.G. Caulton J. Am. Chem. Soc. 122 2000 8916 8931
97. J. Yuan, R. P. Hughes, Unpublished observations.
98. C. J. Bourgeois, J. Yuan, R. P. Hughes, Unpublished observations.
99. R.P. Hughes, A. Williamson, R.D. Sommer, and A.L. Rheingold J. Am. Chem. Soc. 123 2001 7443 7444
100. R.P. Hughes, R.B. Laritchev, A. Williamson, C.D. Incarvito, L.N. Zakharov, and A.L. Rheingold Organometallics 21 2002 4873 4885
101. R.P. Hughes, R.B. Laritchev, A. Williamson, C.D. Incarvito, L.N. Zakharov, and A.L. Rheingold Organometallics 22 2003 2134 2141
102. H. Huang, R.P. Hughes, C.R. Landis, and A.L. Rheingold J. Am. Chem. Soc. 128 2006 7454 7455
103. H. Huang, R.P. Hughes, and A.L. Rheingold Organometallics 29 2010 1948 1955
104. H. Huang, R.P. Hughes, Unpublished observations.
105. D. Lentz, and S. Willemsen Organometallics 18 1999 3962 3964
106. D. Lentz, N. Nickelt, and S. Willemsen Chem. Eur. J. 8 2002 1205 1217
107. R.P. Hughes, R.B. Laritchev, L.N. Zakharov, and A.L. Rheingold J. Am. Chem. Soc. 126 2004 2308 2309
108. F.A. Akkerman, and D. Lentz Angew. Chem. Int. Ed. Eng. 46 2007 4902 4904
109. J. Yuan, R.P. Hughes, J.A. Golen, and A.L. Rheingold Organometallics 29 2010 1942 1947
110. N.D. Ball, J.W. Kampf, and M.S. Sanford J. Am. Chem. Soc. 132 2010 2878 2879
111. N.D. Ball, and M.S. Sanford J. Am. Chem. Soc. 131 2009 3796 3797
112. K.L. Hull, W.Q. Anani, and M.S. Sanford J. Am. Chem. Soc. 128 2006 7134 7135
113. I. Kieltsch, G.G. Dubinina, C. Hamacher, A. Kaiser, J. Torres-Nieto, J.M. Hutchison, A. Klein, Y. Budnikova, and D.A. Vicic Organometallics 29 2010 1451 1456
114. D.Y. Mikhaylov, Y.H. Budnikova, T.V. Gryaznova, D.V. Krivolapov, I.A. Litvinov, D.A. Vicic, and O.G. Sinyashin J. Organomet. Chem. 694 2009 3840 3843
115. G.G. Dubinina, W.W. Brennessel, J.L. Miller, and D.A. Vicic Organometallics 27 2008 3933 3938
116. G.G. Dubinina, H. Furutachi, and D.A. Vicic J. Am. Chem. Soc. 2008 ACS ASAP
117. T. Furuya, D. Benitez, E. Tkatchouk, A.E. Strom, P. Tang, W.A. Goddard, and T. Ritter J. Am. Chem. Soc. 132 2010 3793 3807
118. T. Furuya, and T. Ritter J. Am. Chem. Soc. 130 2008 10060 10061
119. T. Furuya, C.A. Kuttruff, and T. Ritter Curr. Opin. Drug Discov. Dev. 11 2008 803 819
120. A. Vigalok Chem. Eur. J. 14 2008 5102 5108
121. S. Piana, I. Devillers, A. Togni, and U. Rothlisberger Angew. Chem. Int. Ed. Eng. 41 2002 979 982
122. A. Togni, A. Mezzetti, P. Barthazy, C. Becker, I. Devillers, R. Frantz, L. Hintermann, M. Perseghini, and M. Sanna Chimia 55 2001 801 805
123. G. Meier, and T. Braun Angew. Chem. Int. Ed. Eng. 48 2009 1546 1548
124. T. Braun, M.A. Salomon, K. Altenhöner, M. Teltewskoi, and S. Hinze Angew. Chem. Int. Ed. Eng. 48 2009 1818 1822
125. T. Braun, F. Wehmeier, and K. Altenhöner Angew. Chem. Int. Ed. Eng. 46 2007 5321 5324
126. T. Braun, D. Noveski, M. Ahijado, and F. Wehmeier Dalton Trans. 2007 3820 3825
127. M.E. Evans, C.L. Burke, S. Yaibuathes, E. Clot, O. Eisenstein, and W.D. Jones J. Am. Chem. Soc. 131 2009 13464 13473
128. R.D. Rieth, W.W. Brennessel, and W.D. Jones Eur. J. Inorg. Chem. 2007 2839 2847
129. H.L. Buckley, T. Wang, O. Tran, and J.A. Love Organometallics 28 2009 2356 2359
130. H.L. Buckley, A.D. Sun, and J.A. Love Organometallics 28 2009 6622 6624
131. T. Wang, and J.A. Love Organometallics 27 2008 3290 3296
132. T. Wang, B.J. Alfonso, and J.A. Love Org. Lett. 9 2007 5629 5631
133. A. Nova, M. Reinhold, R.N. Perutz, S.A. Macgregor, and J.E. McGrady Organometallics 29 2010 1824 1831
134. A. Nova, S. Erhardt, N.A. Jasim, R.N. Perutz, S.A. Macgregor, J.E. McGrady, and A.C. Whitwood J. Am. Chem. Soc. 130 2008 15499 15511
135. R.J. Lindup, T.B. Marder, R.N. Perutz, and A.C. Whitwood Chem. Commun. 2007 3664 3666
136. S. Burling, P.I.P. Elliott, N.A. Jasim, R.J. Lindup, J. McKenna, R.N. Perutz, S.J. Archibald, and A.C. Whitwood Dalton Trans. 2005 3686 3695