Introduction to Tripodal N-Heterocyclic Carbene Iron Complexes

Chapter
Part of the Springer Theses book series (Springer Theses)

Abstract

First introduced to organic chemistry by Doering in the 1950s, and a decade later to organometallic chemistry by Fischer in 1964, carbenes rapidly made their way into all fields of chemistry. These intriguing species have aroused the interest of organic, inorganic, and theoretical chemists like no other single class of molecules. This is most probably due to their exceptional molecular and electronic structures, sophisticated syntheses, and diverse properties, varying from nucleophilic to electrophilic and even to the point of ambiphilic character.

Keywords

Small Molecule Activation Tripodal Ligand Carbene Carbon Nonbonding Orbital Borate Ligand 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    W.v.E. Doering, A.K. Hoffmann, J. Am. Chem. Soc. 76, 6162 (1954)Google Scholar
  2. 2.
    E.O. Fischer, A. Maasboel, Angew. Chem. 76, 645 (1964)CrossRefGoogle Scholar
  3. 3.
    G. Frenking, N. Fröhlich, Chem. Rev. 100, 717 (2000)CrossRefGoogle Scholar
  4. 4.
    W. Kirmse, Carbene, Carbenoide und Carbenanaloge (Verlag Chemie, Weinheim, 1969)Google Scholar
  5. 5.
    W.A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds, vol. 3, 2nd edn. (VCH, Weinheim, 2002), p. 1078Google Scholar
  6. 6.
    F.E. Hahn, M.C. Jahnke, Angew. Chem. Int. Ed. 47, 3122 (2008)CrossRefGoogle Scholar
  7. 7.
    G. Bertrand, Carbene Chemistry: From Fleeting Intermediates to Powerful reagents (Fontis Media S. A. and Marcel Dekker, Lausanne, 2002)CrossRefGoogle Scholar
  8. 8.
    X. Hu, Metal Complexes of Tripodal N-Heterocyclic Carbene Ligands: Synthesis, Structure, Bonding, and Reactivity. PhD thesis, University of California, San Diego (2004)Google Scholar
  9. 9.
    A.J. Arduengo, R. Krafczyk, Chemie in unserer Zeit 32, 6 (1998)CrossRefGoogle Scholar
  10. 10.
    W.W. Schoeller, J. Chem. Soc. Chem. Commun. 124, (1980)Google Scholar
  11. 11.
    D. Bourissou, O. Guerret, F.P. Gabbai, G. Bertrand, Chem. Rev. 100, 39 (2000)CrossRefGoogle Scholar
  12. 12.
    G.B. Schuster, Adv. Phys. Org. Chem. 22, 311 (1986)Google Scholar
  13. 13.
    R. Hoffmann, G.D. Zeiss, G.W. Van Dine, J. Am. Chem. Soc. 90, 1485 (1968)CrossRefGoogle Scholar
  14. 14.
    C.W. Bauschlicher Jr., H.F. Schaefer III, P.S. Bagus, J. Am. Chem. Soc. 99, 7106 (1977)CrossRefGoogle Scholar
  15. 15.
    D. Feller, W.T. Borden, E.R. Davidson, Chem. Phys. Lett. 71, 22 (1980)CrossRefGoogle Scholar
  16. 16.
    J.F. Harrison, J. Am. Chem. Soc. 93, 4112 (1971)CrossRefGoogle Scholar
  17. 17.
    J.F. Harrison, R.C. Liedtke, J.F. Liebman, J. Am. Chem. Soc. 101, 7162 (1979)CrossRefGoogle Scholar
  18. 18.
    C.D. Abernethy, G.M. Codd, M.D. Spicer, M.K. Taylor, J. Am. Chem. Soc. 125, 1128 (2003)CrossRefGoogle Scholar
  19. 19.
    J.B. Dumas, E.M. Péligot, Annales de chimie et de physique 58, 5 (1835)Google Scholar
  20. 20.
    A. Geuther, Annalen der Chemie und Pharmacie 123, 121 (1862)CrossRefGoogle Scholar
  21. 21.
    H. Scheibler, Chem. Ber. 59, 1022 (1926)CrossRefGoogle Scholar
  22. 22.
    M. Schmeisser, H. Schroeter, H. Schilder, J. Massonne, F. Rosskopf, Chem. Ber. 95, 1648 (1962)CrossRefGoogle Scholar
  23. 23.
    M. Schmeisser, H. Schroter, Angew. Chem. 72, 349 (1960)CrossRefGoogle Scholar
  24. 24.
    H.W. Wanzlick, E. Schikora, Angew. Chem. 72, 494 (1960)CrossRefGoogle Scholar
  25. 25.
    H.J. Schoenherr, H.W. Wanzlick, Justus Liebigs Annalen der Chemie 731, 176 (1970)CrossRefGoogle Scholar
  26. 26.
    A.J. Arduengo III, R.L. Harlow, M. Kline, J. Am. Chem. Soc. 113, 361 (1991)CrossRefGoogle Scholar
  27. 27.
    T. Weskamp, V.P.W. Böhm, W.A. Herrmann, J. Organomet. Chem. 600, 12 (2000)CrossRefGoogle Scholar
  28. 28.
    C.M. Crudden, D.P. Allen, Coord. Chem. Rev. 248, 2247 (2004)CrossRefGoogle Scholar
  29. 29.
    S.P. Nolan (ed.), N-Heterocyclic Carbenes in Synthesis (Wiley-VCH, Weinheim, 2006)Google Scholar
  30. 30.
    F. Glorius, N-Heterocyclic Carbenes in Transition Metal Catalysis, vol. 21 (Springer, Berlin, 2007), p. 1Google Scholar
  31. 31.
    A.C. Hillier, G.A. Grasa, M.S. Viciu, H.M. Lee, C. Yang, S.P. Nolan, J. Organomet. Chem. 653, 69 (2002)CrossRefGoogle Scholar
  32. 32.
    E.A.B. Kantchev, C.J. O’Brien, M.G. Organ, Angew. Chem. Int. Ed. 46, 2768 (2007)CrossRefGoogle Scholar
  33. 33.
    A. Fürstner, Angew. Chem. Int. Ed. 39, 3012 (2000)CrossRefGoogle Scholar
  34. 34.
    S.J. Connon, S. Blechert, Angew. Chem. Int. Ed. 42, 1900 (2003)CrossRefGoogle Scholar
  35. 35.
    H. Clavier, K. Grela, A. Kirschning, M. Mauduit, S.P. Nolan, Angew. Chem. Int. Ed. 46, 6786 (2007)CrossRefGoogle Scholar
  36. 36.
    J.K. Huang, E.D. Stevens, S.P. Nolan, J.L. Petersen, J. Am. Chem. Soc. 121, 2674 (1999)CrossRefGoogle Scholar
  37. 37.
    W.A. Herrmann, Angew. Chem. Int. Ed. 41, 1290 (2002)CrossRefGoogle Scholar
  38. 38.
    W.A. Herrmann, M. Elison, J. Fischer, C. Kocher, G.R.J. Artus, Angew. Chem. Int. Ed. 34, 2371 (1995)CrossRefGoogle Scholar
  39. 39.
    W.A. Herrmann, C. Kocher, Angew. Chem. Int. Ed. 36, 2163 (1997)Google Scholar
  40. 40.
    W.A. Herrmann, Angew. Chem. Int. Ed. 41, 1290 (2002)CrossRefGoogle Scholar
  41. 41.
    L. Sacconi, I. Bertini, J. Am. Chem. Soc. 90, 5443 (1968)CrossRefGoogle Scholar
  42. 42.
    X.L. Hu, I. Castro-Rodriguez, K. Olsen, K. Meyer, Organometallics 23, 755 (2004)CrossRefGoogle Scholar
  43. 43.
    D.M. Khramov, V.M. Lynch, C.W. Bielawski, Organometallics 26, 6042 (2007)CrossRefGoogle Scholar
  44. 44.
    L. Mercs, G.l. Labat, A. Neels, A. Ehlers, M. Albrecht, Organometallics 25, 5648 (2006)Google Scholar
  45. 45.
    M.D. Sanderson, J.W. Kamplain, C.W. Bielawski, J. Am. Chem. Soc. 128, 16514 (2006)CrossRefGoogle Scholar
  46. 46.
    H. Jacobsen, A. Correa, C. Costabile, L. Cavallo, J. Organomet. Chem. 691, 4350 (2006)CrossRefGoogle Scholar
  47. 47.
    D. Nemcsok, K. Wichmann, G. Frenking, Organometallics 23, 3640 (2004)CrossRefGoogle Scholar
  48. 48.
    R. Tonner, G. Heydenrych, G. Frenking, Chem Asian J 2, 1555 (2007)Google Scholar
  49. 49.
    N.M. Scott, R. Dorta, E.D. Stevens, A. Correa, L. Cavallo, S.P. Nolan, J. Am. Chem. Soc. 127, 3516 (2005)CrossRefGoogle Scholar
  50. 50.
    H. Jacobsen, A. Correa, A. Poater, C. Costabile, L. Cavallo, Coord. Chem. Rev. 253, 687 (2009)CrossRefGoogle Scholar
  51. 51.
    J. Chatt, L.A. Duncanson, J. Chem. Soc. 2939 (1953)Google Scholar
  52. 52.
    R.R. Schrock, Acc. Chem. Res. 30, 9 (1997)CrossRefGoogle Scholar
  53. 53.
    T.A. Betley, J.C. Peters, Inorg. Chem. 42, 5074 (2003)CrossRefGoogle Scholar
  54. 54.
    H.A. Mayer, W.C. Kaska, Chem. Rev. 94, 1239 (1994)CrossRefGoogle Scholar
  55. 55.
    S. Trofimenko, J. Chem. Educ. 82, 1715 (2005)CrossRefGoogle Scholar
  56. 56.
    N. Burzlaff, Angew. Chem. Int. Ed. 48, 5580 (2009)CrossRefGoogle Scholar
  57. 57.
    S. Trofimenko, J. Am. Chem. Soc. 88, 1842 (1966)CrossRefGoogle Scholar
  58. 58.
    S. Trofimenko, Prog. Inorg. Chem. 34, 115 (1986)CrossRefGoogle Scholar
  59. 59.
    S. Trofimenko, Chem. Rev. 93, 943 (1993)CrossRefGoogle Scholar
  60. 60.
    N. Kitajima, Y. Moro-oka, Chem. Rev. 94, 737 (1994)CrossRefGoogle Scholar
  61. 61.
    D.L. Reger, C.A. Little, A.L. Rheingold, M. Lam, L.M. Liable-Sands, B. Rhagitan, T. Concolino, A. Mohan, G.J. Long, V. Briois, F. Grandjean, Inorg. Chem. 40, 1508 (2001)CrossRefGoogle Scholar
  62. 62.
    D.L. Reger, C.A. Little, A.L. Rheingold, R. Sommer, G.J. Long, Inorg. Chim. Acta 316, 65 (2001)CrossRefGoogle Scholar
  63. 63.
    H. Pfeiffer, A. Rojas, J. Niesel, U. Schatzschneider, Dalton Trans. (22), 4292 (2009)Google Scholar
  64. 64.
    R.R. Schrock, D.V. Yandulov, Science 301, 76 (2003)CrossRefGoogle Scholar
  65. 65.
    R.A. Kinney, D.G.H. Hetterscheid, B.S. Hanna, R.R. Schrock, B.M. Hoffman, Inorg. Chem. 49, 704 (2009)CrossRefGoogle Scholar
  66. 66.
    M.R. Reithofer, R.R. Schrock, P. Müller, J. Am. Chem. Soc. 132, 8349 (2010)CrossRefGoogle Scholar
  67. 67.
    D.C. Lacy, R. Gupta, K.L. Stone, J. Greaves, J.W. Ziller, M.P. Hendrich, A.S. Borovik, J. Am. Chem. Soc. 132, 12188 (2010)Google Scholar
  68. 68.
    C.E. MacBeth, A.P. Golombek, V.G. Young Jr., C. Yang, K. Kuczera, M.P. Hendrich, A.S. Borovik, Science 289, 938 (2000)CrossRefGoogle Scholar
  69. 69.
    D.M. Jenkins, T.A. Betley, J.C. Peters, J. Am. Chem. Soc. 124, 11238 (2002)CrossRefGoogle Scholar
  70. 70.
    T.A. Betley, J.C. Peters, J. Am. Chem. Soc. 126, 6252 (2004)CrossRefGoogle Scholar
  71. 71.
    S.D. Brown, T.A. Betley, J.C. Peters, J. Am. Chem. Soc. 125, 322 (2003)CrossRefGoogle Scholar
  72. 72.
    M.P. Hendrich, W. Gunderson, R.K. Behan, M.T. Green, M.P. Mehn, T.A. Betley, C.C. Lu, J.C. Peters, Proc. Natl. Acad. Sci. 103, 17107 (2006)CrossRefGoogle Scholar
  73. 73.
    H.V.R. Dias, W.C. Jin, Tetrahedron Lett. 35, 1365 (1994)CrossRefGoogle Scholar
  74. 74.
    H. Nakai, Y. Tang, P. Gantzel, K. Meyer, Chem. Commun. (1), 24 (2003)Google Scholar
  75. 75.
    U. Kernbach, M. Ramm, P. Luger, W.P. Fehlhammer, Angew. Chem. Int. Ed. 35, 310 (1996)CrossRefGoogle Scholar
  76. 76.
    R. Fränkel, C. Birg, U. Kernbach, T. Habereder, H. Nöth, W.P. Fehlhammer, Angew. Chem. Int. Ed. 40, 1907 (2001)CrossRefGoogle Scholar
  77. 77.
    R. Fränkel, U. Kernbach, M. Bakola-Christianopoulou, U. Plaia, M. Suter, W. Ponikwar, H. Nöth, C. Moinet, W.P. Fehlhammer, J. Organomet. Chem. 617–618, 530 (2001)CrossRefGoogle Scholar
  78. 78.
    J.J. Scepaniak, J.A. Young, R.P. Bontchev, J.M. Smith, Angew. Chem. Int. Ed. 48, 3158 (2009)Google Scholar
  79. 79.
    J.J. Scepaniak, M.D. Fulton, R.P. Bontchev, E.N. Duesler, M.L. Kirk, J.M. Smith, J. Am. Chem. Soc. 130, 10515 (2008)CrossRefGoogle Scholar
  80. 80.
    K. Chen, M. Costas, J. Kim, A.K. Tipton, L. Que, J. Am. Chem. Soc. 124, 3026 (2002)CrossRefGoogle Scholar
  81. 81.
    M. Costas, M.P. Mehn, M.P. Jensen, L. Que Jr., Chem. Rev. 104, 939 (2004)CrossRefGoogle Scholar
  82. 82.
    J.-U. Rohde, J.-H. In, M.H. Lim, W.W. Brennessel, M.R. Bukowski, A. Stubna, E. Münck, W. Nam, L. Que, Science 299, 1037 (2003)CrossRefGoogle Scholar
  83. 83.
    K. Meyer, E. Bill, B. Mienert, T. Weyhermüller, K. Wieghardt, J. Am. Chem. Soc. 121, 4859 (1999)CrossRefGoogle Scholar
  84. 84.
    M. Aliaga-Alcalde, S.D. George, B. Mienert, E. Bill, K. Wieghardt, F. Neese, Angew. Chem. Int. Ed. 44, 2908 (2005)CrossRefGoogle Scholar
  85. 85.
    C.A. Grapperhaus, B. Mienert, E. Bill, T. Weyhermüller, K. Wieghardt, Inorg. Chem. 39, 5306 (2000)CrossRefGoogle Scholar
  86. 86.
    J.F. Berry, E. Bill, E. Bothe, S.D. George, B. Mienert, F. Neese, K. Wieghardt, Science 312, 1937 (2006)CrossRefGoogle Scholar
  87. 87.
    G. Ertl, Chem. Rec. 1, 33 (2001)CrossRefGoogle Scholar
  88. 88.
    B.M. Hoffman, D.R. Dean, L.C. Seefeldt, Acc. Chem. Res. 42, 609 (2009)CrossRefGoogle Scholar
  89. 89.
    G. Ertl, Angew. Chem. Int. Ed. 29, 1219 (1990)CrossRefGoogle Scholar
  90. 90.
    O. Einsle, F.A. Tezcan, S.L.A. Andrade, B. Schmid, M. Yoshida, J.B. Howard, D.C. Rees, Science 297, 1696 (2002)CrossRefGoogle Scholar
  91. 91.
    D. Lukoyanov, V. Pelmenschikov, N. Maeser, M. Laryukhin, T.-C. Yang, L. Noodleman, D.R. Dean, D.A. Case, L.C. Seefeldt, B.M. Hoffman, Inorg. Chem. 46, 11437 (2007)CrossRefGoogle Scholar
  92. 92.
    T.-C. Yang, N.K. Maeser, M. Laryukhin, H.-I. Lee, D.R. Dean, L.C. Seefeldt, B.M. Hoffman, J. Am. Chem. Soc. 127, 12804 (2005)CrossRefGoogle Scholar
  93. 93.
    D.S. Scholl, J.A. Steckel, Density Functional Theory: A Practical Introduction (Wiley, Hoboken, 2009)CrossRefGoogle Scholar
  94. 94.
    K. Meyer, J. Bendix, N. Metzler-Nolte, T. Weyhermüller, K. Wieghardt, J. Am. Chem. Soc. 120, 7260 (1998)CrossRefGoogle Scholar
  95. 95.
    C.J. Ballhausen, H.B. Gray, Inorg. Chem. 1, 111 (1962)CrossRefGoogle Scholar
  96. 96.
    J.R. Winkler, H.B. Gray, J. Am. Chem. Soc. 105, 1373 (1983)CrossRefGoogle Scholar
  97. 97.
    J.R. Winkler, H.B. Gray, Inorg. Chem. 24, 346 (1985)CrossRefGoogle Scholar
  98. 98.
    J. Bendix, J. Am. Chem. Soc. 125, 13348 (2003)CrossRefGoogle Scholar
  99. 99.
    K. Meyer, J. Bendix, E. Bill, T. Weyhermüller, K. Wieghardt, Inorg. Chem. 37, 5180 (1998)CrossRefGoogle Scholar
  100. 100.
    A. Niemann, U. Bossek, G. Haselhorst, K. Wieghardt, B. Nuber, Inorg. Chem. 35, 906 (1996)CrossRefGoogle Scholar
  101. 101.
    J. Bendix, K. Meyer, T. Weyhermüller, E. Bill, N. Metzler-Nolte, K. Wieghardt, Inorg. Chem. 37, 1767 (1998)CrossRefGoogle Scholar
  102. 102.
    J. Bendix, R.J. Deeth, T. Weyhermüller, E. Bill, K. Wieghardt, Inorg. Chem. 39, 930 (2000)CrossRefGoogle Scholar
  103. 103.
    M. Aliaga-Alcalde, S.D. George, B. Mienert, E. Bill, K. Wieghardt, F. Neese, Angew. Chem. Int. Ed. 44, 2908 (2005)CrossRefGoogle Scholar
  104. 104.
    T.A. Betley, J.C. Peters, J. Am. Chem. Soc. 125, 10782 (2003)CrossRefGoogle Scholar
  105. 105.
    D.M. Jenkins, A.J. Di Bilio, M.J. Allen, T.A. Betley, J.C. Peters, J. Am. Chem. Soc. 124, 15336 (2002)Google Scholar
  106. 106.
    C.M. Thomas, N.P. Mankad, J.C. Peters, J. Am. Chem. Soc. 128, 4956 (2006)CrossRefGoogle Scholar
  107. 107.
    C.M. Thomas, J.C. Peters, Angew. Chem. Int. Ed. 45, 776 (2006)CrossRefGoogle Scholar
  108. 108.
    X. Hu, K. Meyer, J. Am. Chem. Soc. 126, 16322 (2004)CrossRefGoogle Scholar
  109. 109.
    C.S. Vogel, F.W. Heinemann, J. Sutter, C. Anton, K. Meyer, An iron nitride complex. Angew. Chem. Int. Ed. 47, 2681–2684 (2008)CrossRefGoogle Scholar
  110. 110.
    C.S. Vogel, F.W. Heinemann, M.M. Khusniyarov, K. Meyer, Unexpected reactivity resulting from modifications of the ligand periphery: synthesis, structure, and spectroscopic properties of iron complexes of new tripodal N-heterocyclic carbene (NHC) ligands: invited article dedicated to Prof. Arnold Rheingold. Inorg. Chim. Acta 364, 226–236 (2010)Google Scholar
  111. 111.
    J.J. Scepaniak, C.S. Vogel, M.M. Khusniyarov, F.W. Heinemann, K. Meyer, J.M. Smith, Synthesis, structure, and reactivity of an iron(V) nitride. Science 331, 1049–1052 (2011)CrossRefGoogle Scholar
  112. 112.
    J.J. Scepaniak, T.D. Harris, C.S. Vogel, J. Sutter, K. Meyer, J.M. Smith, Spin crossover in a four-coordinate iron(II) complex. J. Am. Chem. Soc. 133, 3824–3827 (2011)CrossRefGoogle Scholar

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© Springer-Verlag Berlin Heidelberg 2012

Authors and Affiliations

  1. 1.Department of Chemistry and Pharmacy, Inorganic ChemistryFriedrich-Alexander-University Erlangen-NurembergErlangenGermany

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