N-Heterocyclic carbene bonding to cobalt porphyrin complexes

Inorganica Chimica Acta

Volumn 380, Issue 1, 2012, Pages 90-95

  Albrecht, Martin ^a   Maji, Pathik ^a   Häusl, Christina ^a   Monney, Angle ^a   Müller Bunz, Helge ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Cobalt; Imidazole; Ligand substitution; N Heterocyclic carbene; Porphyrin; Steric strain

Indexed keywords

EID: 84856232871     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2011.08.039     Document Type: Article

References (88)

1. A.J. Arduengo, and G. Bertrand Chem. Rev. 109 2009 3209
2. S.P. Nolan N-Heterocyclic Carbenes in Synthesis 2006 Wiley-VCH Weinheim
3. F.A. Glorius Top. Organomet. Chem. 21 2007 1
4. C.S.J. Cazin N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis 2010 Springer Berlin
5. S. Diez-Gonzalez N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools 2011 RSC Catalysis Series Cambridge, UK
6. W.A. Herrmann Angew. Chem., Int. Ed. 41 2002 1290
7. A.J. Arduengo Acc. Chem. Res. 32 1999 913
8. D. Bourissou, O. Guerret, F.P. Gabbai, and G. Bertrand Chem. Rev. 100 2000 39
9. F.E. Hahn, and M.C. Jahnke Angew. Chem., Int. Ed. 47 2008 3122
10. D. Martin, M. Soleilhavoup, and G. Bertrand Chem. Sci. 2 2011 389
11. R.G. Pearson J. Am. Chem. Soc. 85 1963 3533
12. R.G. Pearson Science 14 1966 172
13. M. Tafipolsky, W. Scherer, K. Oefele, G. Artus, B. Pedersen, W.A. Herrmann, and G.S. McGrady J. Am. Chem. Soc. 124 2002 5865
14. X. Hu, Y. Tang, P. Gantzel, and K. Meyer Organometallics 22 2003 612
15. M.-T. Lee, and C.-H. Hu Organometallics 23 2004 976
16. D. Nemcsok, K. Wichmann, and G. Frenking Organometallics 23 2004 3640
17. N.M. Scott, R. Dorta, E.D. Stevens, A. Correa, L. Cavallo, and S.P. Nolan J. Am. Chem. Soc. 127 2005 3516
18. E.F. Penka, C.W. Schläpfer, M. Atanasov, M. Albrecht, and C. Daul J. Organomet. Chem. 692 2007 5709
19. V. Lavallo, and R.H. Grubbs Science 326 2009 559
20. N.M. Scott, H. Clavier, P. Jahjoor, E.D. Stevens, and S.P. Nolan Organometallics 27 2008 3181
21. Irreversible dissociation has been frequently observed and can constitute a critical step in catalyst activation. For detailed studies from our laboratories in this direction, see: C. Gandolfi, M. Heckenroth, A. Neels, G. Laurenczy, and M. Albrecht Organometallics 28 2009 5112
22. M. Heckenroth, V. Khlebnikov, A. Neels, P. Schurtenberger, and M. Albrecht ChemCatChem 3 2011 167
23. P.L. Arnold, and I.J. Casely Chem. Rev. 109 2009 3599
24. For earth alkali and alkali metal NHC complexes, see: A.J. Arduengo, M. Tamm, J.C. Calabrese, F. Davidson, and W.J. Marshall Chem. Lett. 1999 1021
25. R.W. Alder, M.E. Blake, C. Bortolotti, S. Bufali, C.P. Butts, E. Linehan, J.M. Oliva, A.G. Orpen, and M.J. Quayle Chem. Commun. 1999 241
26. R. Fränkel, C. Birg, U. Kernbach, T. Habereder, H. Nöth, and W.P. Fehlhammer Angew. Chem., Int. Ed. 40 2001 1907
27. P.L. Arnold, S.A. Mungur, A.J. Blake, and C. Wilson Angew. Chem., Int. Ed. 42 2003 5981
28. A. Stasch, S.P. Sarish, H.W. Roesky, K. Meindl, F. Dall'Antonia, T. Schulz, and D. Stalke Chem. Asian J. 4 2009 1451
29. M. Arrowsmith, M.S. Hill, D.J. MacDougall, and M.F. Mahon Angew. Chem., Int. Ed. 48 2009 4013
30. A.R. Kennedy, R.E. Mulvey, and S.D. Robertson Dalton Trans. 39 2010 9091
31. For selected recent reports on p-block NHC complexes, see: Y. Wang, B. Quilian, P.R. Wei, C.S. Wannere, Y. Xie, R.B. King, H.F. Schaefer, P.V. Schleyer, and G.H. Robinson J. Am. Chem. Soc. 129 2007 12412
32. Y. Wang, B. Quilian, P.R. Wei, Y. Xie, R.B. King, H.F. Schaefer, P.V. Schleyer, and G.H. Robinson Science 321 2008 1069
33. S.J. Bonyhady, D. Collis, G. Frenking, N. Holzmann, C. Jones, and A. Stasch Nat. Chem. 2 2010 865
34. R.S. Ghadwal, H.W. Roesky, M. Granitzka, and D. Stalke J. Am. Chem. Soc. 132 2010 10018
35. R.C. Fischer, and P.P. Power Chem. Rev. 110 2010 3877
36. For examples of group 3-7 NHC chemistry, see: M.A. Huertos, J. Perez, L. Riera, J. Diaz, and R. Lopez Angew. Chem., Int. Ed. 49 2010 6409
37. D.S. McGuinness, V.C. Gibson, D.F. Wass, and J.W. Steed J. Am. Chem. Soc. 125 2003 12716
38. W. Zhang, and K. Nomura Organometallics 27 2008 6400
39. S. Bellemin-Laponnaz, R. Welter, L. Brelot, and S. Dagorne J. Organomet. Chem. 694 2009 604
40. D. Patel, S.T. Liddle, S.A. Mungur, M. Rodden, A.J. Blake, and P.L. Arnold Chem. Commun. 2006 1124
41. S. Diez-Gonzalez, N. Marion, and S.P. Nolan Chem. Rev. 109 2009 3612
42. C. Samojlowicz, M. Bieniek, and K. Grela Chem. Rev. 109 2009 3708
43. O. Schuster, L. Yang, H.G. Raubenheimer, and M. Albrecht Chem. Rev. 109 2009 3445
44. G.C. Vougioukalakis, and R.H. Grubbs Chem. Rev. 110 2010 1746
45. J.C. Garrison, and W.J. Youngs Chem. Rev. 105 2005 3978
46. M.M. Diaz-Requejo, and P.J. Perez Chem. Rev. 108 2008 3379
47. J.C.Y. Lin, R.T.W. Huang, C.S. Lee, A. Bhattacharyya, W.S. Hwang, and I.J.B. Lin Chem. Rev. 109 2009 3561
48. S.P. Nolan Acc. Chem. Res. 44 2011 91
49. For selected Fe-NHC work, see: M.F. Lappert J. Organomet. Chem. 358 1972 185
50. D. Rieger, S.D. Lotz, U. Kernbach, C. Andre, J. Bertran-Nadal, and W.P. Fehlhammer J. Organomet. Chem. 491 1995 135
51. H.G. Raubenheimer, F. Scott, S. Cronje, P.H. Rooyen, and K. Psotta J. Chem. Soc., Dalton Trans. 999 1992 1009
52. P. Buchgraber, L. Toupet, and V. Guerchais Organometallics 22 2003 5144
53. L. Mercs, G. Labat, A. Neels, A. Ehlers, and M. Albrecht Organometallics 25 2006 5648
54. For selected Ni-NHC work, see: R.E. Douthwaite, M.L.H. Green, P.J. Silcock, and P.T. Gomes Organometallics 20 2001 2611
55. V. Ritleng, C. Barth, E. Brenner, S. Milosevic, and M.J. Chetcuti Organometallics 27 2008 4223
56. X. Zhang, B. Liu, A. Liu, W. Xie, and W. Chen Organometallics 28 2009 1336
57. E. Stander-Grobler, O. Schuster, G. Heydenrych, S. Cronje, E. Tosh, M. Albrecht, G. Frenking, and H.G. Raubenheimer Organometallics 29 2010 5821
58. K. Zhang, M. Conda Sheridan, S.R. Cooke, and J. Louie Organometallics 30 2011 2546
59. M.F. Lappert, and P.L. Pye J. Chem. Soc., Dalton Trans. 999 1977 2172
60. A.W. Coleman, P.B. Hitchcock, M.F. Lappert, R.K. Maskell, and J.H. Müller J. Organomet. Chem. 29 1985 173
61. X. Hu, I. Castro-Rodriguez, and K. Meyer J. Am. Chem. Soc. 126 2004 13464
62. X. Hu, and K. Meyer J. Am. Chem. Soc. 126 2004 16322
63. S.E. Gibson, C. Johnstone, J.A. Loch, J.W. Steed, and A. Stevenazzi Organometallics 22 2003 5374
64. H. van Rensburg, R.P. Tooze, D.F. Foster, and A.M.Z. Slawin Inorg. Chem. 43 2004 2468
65. H. van Rensburg, R.P. Tooze, D.F. Foster, and S. Otto Inorg. Chem. 46 2007 1963
66. A.M. Poutlon, S.D.R. Christie, R. Fryatt, S.H. Dale, and M.R.J. Elsegood Synlett 999 2004 2103
67. S.A. Llewellyn, M.L.H. Green, and A.R. Cowley Dalton Trans. 999 2006 4164
68. J. Li, S. Merkel, J. Henn, K. Meindl, A. Dring, H.W. Roesky, R.S. Ghadwal, and D. Stalke Inorg. Chem. 49 2010 775
69. K.M. Kadish, K.M. Smith, and R. Guilard The Porphyrin Handbook 2000 Academic Press San Diego, CA
70. J.P. Collman, J.I. Brauman, K.M. Doxsee, T.R. Halbert, S.E. Hayes, and K.S. Suslick J. Am. Chem. Soc. 100 1978 2761
71. H. Bang, J.O. Edwards, J. Kim, R.G. Lawler, K. Reynolds, W.J. Ryan, D.A. Sweigart, J. Am. Chem. Soc. 114 (1992) 2843.
72. M. Dennis, and P.E. Kolattukudy Proc. Natl. Acad. Sci. USA 89 1992 5306
73. P. Chen, M.H. Chisholm, J.C. Gallucci, X. Zhang, and Z. Zhou Inorg. Chem. 44 2005 2588
74. A.M. Voutchkova, M. Feliz, E. Clot, O. Eisenstein, and R.H. Crabtree J. Am. Chem. Soc. 129 2007 12834
75. A. Mahmood, H. Liu, J.G. Jones, J.O. Edwards, and D.A. Sweigart Inorg. Chem. 27 1988 2149
76. H. Zhang, U. Simonis, and F.A. Walker J. Am. Chem. Soc. 112 1990 6124
77. M. Nakamura, and A. Ikezaki Chem. Lett. 1995 733
78. W.R. Scheidt, and D.M. Chipman J. Am. Chem. Soc. 108 1986 1163
79. P.N. Dwyer, P. Madura, and W.R. Scheidt J. Am. Chem. Soc. 96 1974 4815
80. W.R. Scheidt Acc. Chem. Res. 10 1977 339
81. A.L. Balch, J.J. Watkins, and D.J. Doonan Inorg. Chem. 18 1979 1228
82. H.M. Goff J. Am. Chem. Soc. 103 1981 3714
83. K.I. Hagen, C.M. Schwab, J.O. Edwards, and D.A. Sweigart Inorg. Chem. 25 1986 978
84. K.I. Hagen, C.M. Schwab, J.O. Edwards, J.G. Jones, R.G. Lawler, and D.A. Sweigart J. Am. Chem. Soc. 110 1988 7024
85. T. Sakurai, K. Yamamoto, H. Naito, and N. Nakamoto Bull. Chem. Soc. Jpn. 49 1976 3042
86. Program CrysalisPro Version 1.171.33.55, Oxford Diffraction Limited, 2010.
87. G.M. Sheldrick Acta Crystallogr., Sect. A64 2008 112
88. H.D. Flack Acta Crystallogr., Sect. A39 1983 876