Synthesis of trifluoroborate functionalised imidazolium salts as precursors to weakly coordinating bidentate NHC ligands

Inorganica Chimica Acta

Volumn 369, Issue 1, 2011, Pages 180-189

  Gott, Andrew L ^a   Piers, Warren E ^a   McDonald, Robert ^b   Parvez, Masood ^a  

^a UNIVERSITY OF CALGARY   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Bidentate; Fluorination; Hemilability; N heterocyclic carbene; Rhodium; Trifluoroborate

Indexed keywords

CHELATION; COMPLEXATION; CROWN ETHERS; FLUORINATION; HALOGENATION; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; POTASSIUM COMPOUNDS; RHODIUM; SALTS;

BIDENTATE; COORDINATE COMPLEXES; DEPROTECTION; HEMILABILITY; IMIDAZOLIUM SALT; N-HETEROCYCLIC CARBENES; ONE-POT REACTION; TRIFLUOROBORATE;

RHODIUM COMPOUNDS;

EID: 79953873163     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2010.12.030     Document Type: Article

References (93)

1. A.J. Arduengo, R.L. Harlow, and M. Kline J. Am. Chem. Soc. 113 1991 361
2. A.J. Arduengo Acc. Chem. Res. 32 1999 913
3. P. de Fremont, N. Marion, and S.P. Nolan Coord. Chem. Rev. 253 2009 862
4. H. Clavier, and S.P. Nolan Chem. Commun. 46 2010 841
5. D.G. Gusev Organometallics 28 2009 6458
6. R. Tonner, and G. Frenking Organometallics 28 2009 3901
7. R.A. Kelly, H. Clavier, S. Giudice, N.M. Scott, E.D. Stevens, J. Bordner, I. Samardjiev, C.D. Hoff, L. Cavallo, and S.P. Nolan Organometallics 27 2008 202
8. G. Song, Y. Zhang, and X. Li Organometallics 27 2008 1936
9. S. Leuthausser, D. Schwarz, and H. Plenio Chem. Eur. J. 13 2007 7195
10. W.A. Herrmann, J. Schutz, G.D. Frey, and E. Herdtweck Organometallics 25 2006 2437
11. R. Dorta, E.D. Stevens, N.M. Scott, C. Costabile, L. Cavallo, C.D. Hoff, and S.P. Nolan J. Am. Chem. Soc. 127 2005 2485
12. C. Samojlowicz, M. Bieniek, and K. Grela Chem. Rev. 109 2009 3708
13. S. Monfette, and D.E. Fogg Chem. Rev. 109 2009 3783
14. M.S. Sanford, J.A. Love, and R.H. Grubbs Organometallics 20 2001 5314
15. S.B. Garber, J.S. Kingsbury, B.L. Gray, and A.H. Hoveyda J. Am. Chem. Soc. 122 2000 8168
16. J.S. Kingsbury, J.P.A. Harrity, P.J. Bonitatebus, and A.H. Hoveyda J. Am. Chem. Soc. 121 1999 791
17. M. Scholl, S. Ding, C.W. Lee, and R.H. Grubbs Org. Lett. 1 1999 953
18. N. Marion, and S.P. Nolan Acc. Chem. Res. 41 2008 1440
19. S. Wurtz, and F. Glorius Acc. Chem. Res. 41 2008 1523
20. E.A.B. Kantchev, C.J. O'Brien, and M.G. Organ Angew. Chem., Int. Ed. 46 2007 2768
21. S. Diez-Gonzalez, N. Marion, and S.P. Nolan Chem. Rev. 109 2009 3612
22. O. Schuster, L.R. Yang, H.G. Raubenheimer, and M. Albrecht Chem. Rev. 109 2009 3445
23. D. McGuinness Dalton Trans. 2009 6915
24. D. Enders, O. Niemeier, and A. Henseler Chem. Rev. 107 2007 5605
25. V. Cesar, S. Bellemin-Laponnaz, and L.H. Gade Chem. Soc. Rev. 33 2004 619
26. S.P. Nolan, N-Heterocyclic Carbenes In Synthesis, Wiley-VCH, 2006.
27. H. Jacobsen, A. Correa, A. Poater, C. Costabile, and L. Cavallo Coord. Chem. Rev. 253 2009 2784
28. O. Kuhl Chem. Soc. Rev. 36 2007 592
29. S.T. Liddle, I.S. Edworthy, and P.L. Arnold Chem. Soc. Rev. 36 2007 1732
30. L.R. Moore, S.M. Cooks, M.S. Anderson, H.J. Schanz, S.T. Griffin, R.D. Rogers, M.C. Kirk, and K.H. Shaughnessy Organometallics 25 2006 5151
31. K.S. Lee, and A.H. Hoveyda J. Am. Chem. Soc. 132 2010 2898
32. K. Akiyama, F. Gao, and A.H. Hoveyda Angew. Chem., Int. Ed. 49 2010 419
33. Y.M. Lee, and A.H. Hoveyda J. Am. Chem. Soc. 131 2009 3160
34. Y. Lee, B. Li, and A.H. Hoveyda J. Am. Chem. Soc. 131 2009 11625
35. Y. Lee, H. Jang, and A.H. Hoveyda J. Am. Chem. Soc. 131 2009 18234
36. K.S. Lee, and A.H. Hoveyda J. Org. Chem. 74 2009 4455
37. T.L. May, M.K. Brown, and A.H. Hoveyda Angew. Chem., Int. Ed. 47 2008 7358
38. Y. Lee, K. Akiyama, D.G. Gillingham, M.K. Brown, and A.H. Hoveyda J. Am. Chem. Soc. 130 2008 446
39. D.G. Gillingham, and A.H. Hoveyda Angew. Chem., Int. Ed. 46 2007 3860
40. M.K. Brown, T.L. May, C.A. Baxter, and A.H. Hoveyda Angew. Chem., Int. Ed. 46 2007 1097
41. Y. Nagai, T. Kochi, and K. Nozaki Organometallics 28 2009 6131
42. W. Beck, and K. Sunkel Chem. Rev. 88 1988 1405
43. G. Giordano, and R.H. Crabtree Inorg. Synth. 28 1990 88
44. G.M. Sheldrick, sadabs, Program for Area Detector Absorption Correction, Institute for Inorganic Chemistry, University of Gottingen, Germany, 1996.
45. G.M. Sheldrick Acta Crystallogr., Sect. A: Found. Crystallogr. 64 2008 112
46. E. Vedejs, R.W. Chapman, S.C. Fields, S. Lin, and M.R. Schrimpf J. Org. Chem. 60 1995 3020
47. L.F. Groux, T. Weiss, D.N. Reddy, P.A. Chase, W.E. Piers, T. Ziegler, M. Parvez, and J. Benet-Buchholz J. Am. Chem. Soc. 127 2005 1854
48. A.J. Arduengo, R. Krafczyk, R. Schmutzler, H.A. Craig, J.R. Goerlich, W.J. Marshall, and M. Unverzagt Tetrahedron 55 1999 14523
49. A.G. Wenzel, and R.H. Grubbs J. Am. Chem. Soc. 128 2006 16048
50. G.C. Vougioukalakis, and R.H. Grubbs Organometallics 26 2007 2469
51. K. Vehlow, S. Maechling, and S. Blechert Organometallics 25 2006 25
52. N. Hadei, E.A.B. Kantchev, C.J. O'Brien, and M.G. Organ J. Org. Chem. 70 2005 8503
53. A. Furstner, M. Alcarazo, V. Cesar, and C.W. Lehmann Chem. Commun. 2006 2176
54. A. Paczal, A.C. Benyei, and A. Kotschy J. Org. Chem. 71 2006 5969
55. E.M. Leitao, S.R. Dubberley, W.E. Piers, Q. Wu, and R. McDonald Chem. Eur. J. 14 2008 11565
56. S. Saba, A.M. Brescia, and M.K. Kaloustian Tetrahedron Lett. 32 1991 5031
57. S. Hermanek Chem. Rev. 92 1992 325
58. M. Shimizu, Y. Nakahara, and H. Yoshioka Tetrahedron Lett. 26 1985 4207
59. P. Svec, P. Novak, M. Nadvornik, Z. Padelkova, I. Cisarova, L. Kolarova, A. Ruzicka, and J. Holecek J. Fluorine Chem. 128 2007 1390
60. J.C. Garrison, and W.J. Youngs Chem. Rev. 105 2005 3978
61. A.J. Arduengo, J.C. Calabrese, F. Davidson, H.V.R. Dias, J.R. Goerlich, R. Krafczyk, W.J. Marshall, M. Tamm, and R. Schmutzler Helv. Chim. Acta 82 1999 2348
62. A.J. Arduengo, F. Davidson, R. Krafczyk, W.J. Marshall, and R. Schmutzler Monatsh. Chem. 131 2000 251
63. P.L. Arnold, M. Rodden, and C. Wilson Chem. Commun. 2005 1743
64. P.L. Arnold, and S.T. Liddle Organometallics 25 2006 1485
65. S.P. Downing, and A.A. Danopoulos Organometallics 25 2006 1337
66. S.P. Downing, S.C. Guadano, D. Pugh, A.A. Danopoulos, R.M. Bellabarba, M. Hanton, D. Smith, and R.P. Tooze Organometallics 26 2007 3762
67. K.E. Krahulic, H.M. Tuononen, M. Parvez, and R. Roesler J. Am. Chem. Soc. 131 2009 5858
68. T.K. Wood, W.E. Piers, B.A. Keay, and M. Parvez Angew. Chem., Int. Ed. 48 2009 4009
69. D. Holschumacher, T. Bannenberg, C.G. Hrib, P.G. Jones, and M. Tamm Angew. Chem., Int. Ed. 47 2008 7428
70. A.D. Phillips, and P.P. Power Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 61 2005 O291
71. N. Kuhn, R. Fawzi, H. Kotowski, and M. Steimann Z. Kristallogr. - New Cryst. Struct. 212 1997 259
72. N. Kuhn, G. Henkel, T. Kratz, J. Kreutzberg, R. Boese, and A.H. Maulitz Chem. Ber. 126 1993 2041
73. N.Y. Adonin, V.V. Bardin, U. Florke, and H.J. Frohn Z. Anorg. Allg. Chem. 631 2005 2638
74. E. Bernhardt, M. Berkei, H. Willner, and M. Schurmann Z. Anorg. Allg. Chem. 629 2003 677
75. D. Tapu, D.A. Dixon, and C. Roe Chem. Rev. 109 2009 3385
76. D.J. Cardin, M.J. Doyle, and M.F. Lappert J. Chem. Soc., Chem. Commun. 1972 927
77. D.J. Cardin, M.J. Doyle, and M.F. Lappert J. Organomet. Chem. 65 1974 C13
78. B. Cetinkaya, P. Dixneuf, and M.F. Lappert J. Chem. Soc., Dalton Trans. 1974 1827
79. M.J. Doyle, and M.F. Lappert J. Chem. Soc., Chem. Commun. 1974 679
80. M.J. Doyle, M.F. Lappert, G.M. McLaughlin, and J. McMeeking J. Chem. Soc., Dalton Trans. 1974 1494
81. P.B. Hitchcock, M.F. Lappert, and P.L. Pye J. Chem. Soc., Dalton Trans. 1977 2160
82. P.B. Hitchcock, M.F. Lappert, P. Terreros, and K.P. Wainwright J. Chem. Soc., Chem. Commun. 1980 1180
83. A.W. Coleman, P.B. Hitchcock, M.F. Lappert, R.K. Maskell, and J.H. Muller J. Organomet. Chem. 250 1983 C9
84. M.J. Doyle, M.F. Lappert, P.L. Pye, and P. Terreros J. Chem. Soc., Dalton Trans. 1984 2355
85. J.M. Praetorius, and C.M. Crudden Dalton Trans. 2008 4079
86. S. Fantasia, J.L. Petersen, H. Jacobsen, L. Cavallo, and S.P. Nolan Organometallics 26 2007 5880
87. S. Wolf, and H. Plenio J. Organomet. Chem. 694 2009 1487
88. L. Benhamou, V. Cesar, H. Gornitzka, N. Lugan, and G. Lavigne Chem. Commun. 2009 4720
89. A.P. Blum, T. Ritter, and R.H. Grubbs Organometallics 26 2007 2122
90. H. Turkmen, O. Sahin, O. Buyukgungor, and B. Cetinkaya Eur. J. Inorg. Chem. 2006 4915
91. M. Appel, and W. Beck J. Organomet. Chem. 319 1987 C1
92. K. Sunkel, G. Urban, and W. Beck J. Organomet. Chem. 252 1983 187
93. V.V. Grushin, and W.J. Marshall J. Am. Chem. Soc. 126 2004 3068