Skip to main content
SpringerLink
Log in

Introduction to Tripodal N-Heterocyclic Carbene Iron Complexes

  • Chapter
  • First Online:
High- and Low-Valent tris-N-Heterocyclic Carbene Iron Complexes

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

  • 523 Accesses

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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. W.v.E. Doering, A.K. Hoffmann, J. Am. Chem. Soc. 76, 6162 (1954)

    Google Scholar 

  2. E.O. Fischer, A. Maasboel, Angew. Chem. 76, 645 (1964)

    Article  CAS  Google Scholar 

  3. G. Frenking, N. Fröhlich, Chem. Rev. 100, 717 (2000)

    Article  CAS  Google Scholar 

  4. W. Kirmse, Carbene, Carbenoide und Carbenanaloge (Verlag Chemie, Weinheim, 1969)

    Google Scholar 

  5. W.A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds, vol. 3, 2nd edn. (VCH, Weinheim, 2002), p. 1078

    Google Scholar 

  6. F.E. Hahn, M.C. Jahnke, Angew. Chem. Int. Ed. 47, 3122 (2008)

    Article  CAS  Google Scholar 

  7. G. Bertrand, Carbene Chemistry: From Fleeting Intermediates to Powerful reagents (Fontis Media S. A. and Marcel Dekker, Lausanne, 2002)

    Book  Google Scholar 

  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. A.J. Arduengo, R. Krafczyk, Chemie in unserer Zeit 32, 6 (1998)

    Article  CAS  Google Scholar 

  10. W.W. Schoeller, J. Chem. Soc. Chem. Commun. 124, (1980)

    Google Scholar 

  11. D. Bourissou, O. Guerret, F.P. Gabbai, G. Bertrand, Chem. Rev. 100, 39 (2000)

    Article  CAS  Google Scholar 

  12. G.B. Schuster, Adv. Phys. Org. Chem. 22, 311 (1986)

    CAS  Google Scholar 

  13. R. Hoffmann, G.D. Zeiss, G.W. Van Dine, J. Am. Chem. Soc. 90, 1485 (1968)

    Article  CAS  Google Scholar 

  14. C.W. Bauschlicher Jr., H.F. Schaefer III, P.S. Bagus, J. Am. Chem. Soc. 99, 7106 (1977)

    Article  CAS  Google Scholar 

  15. D. Feller, W.T. Borden, E.R. Davidson, Chem. Phys. Lett. 71, 22 (1980)

    Article  CAS  Google Scholar 

  16. J.F. Harrison, J. Am. Chem. Soc. 93, 4112 (1971)

    Article  CAS  Google Scholar 

  17. J.F. Harrison, R.C. Liedtke, J.F. Liebman, J. Am. Chem. Soc. 101, 7162 (1979)

    Article  CAS  Google Scholar 

  18. C.D. Abernethy, G.M. Codd, M.D. Spicer, M.K. Taylor, J. Am. Chem. Soc. 125, 1128 (2003)

    Article  CAS  Google Scholar 

  19. J.B. Dumas, E.M. Péligot, Annales de chimie et de physique 58, 5 (1835)

    Google Scholar 

  20. A. Geuther, Annalen der Chemie und Pharmacie 123, 121 (1862)

    Article  Google Scholar 

  21. H. Scheibler, Chem. Ber. 59, 1022 (1926)

    Article  Google Scholar 

  22. M. Schmeisser, H. Schroeter, H. Schilder, J. Massonne, F. Rosskopf, Chem. Ber. 95, 1648 (1962)

    Article  CAS  Google Scholar 

  23. M. Schmeisser, H. Schroter, Angew. Chem. 72, 349 (1960)

    Article  CAS  Google Scholar 

  24. H.W. Wanzlick, E. Schikora, Angew. Chem. 72, 494 (1960)

    Article  CAS  Google Scholar 

  25. H.J. Schoenherr, H.W. Wanzlick, Justus Liebigs Annalen der Chemie 731, 176 (1970)

    Article  CAS  Google Scholar 

  26. A.J. Arduengo III, R.L. Harlow, M. Kline, J. Am. Chem. Soc. 113, 361 (1991)

    Article  CAS  Google Scholar 

  27. T. Weskamp, V.P.W. Böhm, W.A. Herrmann, J. Organomet. Chem. 600, 12 (2000)

    Article  CAS  Google Scholar 

  28. C.M. Crudden, D.P. Allen, Coord. Chem. Rev. 248, 2247 (2004)

    Article  CAS  Google Scholar 

  29. S.P. Nolan (ed.), N-Heterocyclic Carbenes in Synthesis (Wiley-VCH, Weinheim, 2006)

    Google Scholar 

  30. F. Glorius, N-Heterocyclic Carbenes in Transition Metal Catalysis, vol. 21 (Springer, Berlin, 2007), p. 1

    Google Scholar 

  31. A.C. Hillier, G.A. Grasa, M.S. Viciu, H.M. Lee, C. Yang, S.P. Nolan, J. Organomet. Chem. 653, 69 (2002)

    Article  CAS  Google Scholar 

  32. E.A.B. Kantchev, C.J. O’Brien, M.G. Organ, Angew. Chem. Int. Ed. 46, 2768 (2007)

    Article  CAS  Google Scholar 

  33. A. Fürstner, Angew. Chem. Int. Ed. 39, 3012 (2000)

    Article  Google Scholar 

  34. S.J. Connon, S. Blechert, Angew. Chem. Int. Ed. 42, 1900 (2003)

    Article  CAS  Google Scholar 

  35. H. Clavier, K. Grela, A. Kirschning, M. Mauduit, S.P. Nolan, Angew. Chem. Int. Ed. 46, 6786 (2007)

    Article  CAS  Google Scholar 

  36. J.K. Huang, E.D. Stevens, S.P. Nolan, J.L. Petersen, J. Am. Chem. Soc. 121, 2674 (1999)

    Article  CAS  Google Scholar 

  37. W.A. Herrmann, Angew. Chem. Int. Ed. 41, 1290 (2002)

    Article  CAS  Google Scholar 

  38. W.A. Herrmann, M. Elison, J. Fischer, C. Kocher, G.R.J. Artus, Angew. Chem. Int. Ed. 34, 2371 (1995)

    Article  CAS  Google Scholar 

  39. W.A. Herrmann, C. Kocher, Angew. Chem. Int. Ed. 36, 2163 (1997)

    Google Scholar 

  40. W.A. Herrmann, Angew. Chem. Int. Ed. 41, 1290 (2002)

    Article  CAS  Google Scholar 

  41. L. Sacconi, I. Bertini, J. Am. Chem. Soc. 90, 5443 (1968)

    Article  CAS  Google Scholar 

  42. X.L. Hu, I. Castro-Rodriguez, K. Olsen, K. Meyer, Organometallics 23, 755 (2004)

    Article  Google Scholar 

  43. D.M. Khramov, V.M. Lynch, C.W. Bielawski, Organometallics 26, 6042 (2007)

    Article  CAS  Google Scholar 

  44. L. Mercs, G.l. Labat, A. Neels, A. Ehlers, M. Albrecht, Organometallics 25, 5648 (2006)

    Google Scholar 

  45. M.D. Sanderson, J.W. Kamplain, C.W. Bielawski, J. Am. Chem. Soc. 128, 16514 (2006)

    Article  CAS  Google Scholar 

  46. H. Jacobsen, A. Correa, C. Costabile, L. Cavallo, J. Organomet. Chem. 691, 4350 (2006)

    Article  CAS  Google Scholar 

  47. D. Nemcsok, K. Wichmann, G. Frenking, Organometallics 23, 3640 (2004)

    Article  CAS  Google Scholar 

  48. R. Tonner, G. Heydenrych, G. Frenking, Chem Asian J 2, 1555 (2007)

    Google Scholar 

  49. N.M. Scott, R. Dorta, E.D. Stevens, A. Correa, L. Cavallo, S.P. Nolan, J. Am. Chem. Soc. 127, 3516 (2005)

    Article  CAS  Google Scholar 

  50. H. Jacobsen, A. Correa, A. Poater, C. Costabile, L. Cavallo, Coord. Chem. Rev. 253, 687 (2009)

    Article  CAS  Google Scholar 

  51. J. Chatt, L.A. Duncanson, J. Chem. Soc. 2939 (1953)

    Google Scholar 

  52. R.R. Schrock, Acc. Chem. Res. 30, 9 (1997)

    Article  CAS  Google Scholar 

  53. T.A. Betley, J.C. Peters, Inorg. Chem. 42, 5074 (2003)

    Article  CAS  Google Scholar 

  54. H.A. Mayer, W.C. Kaska, Chem. Rev. 94, 1239 (1994)

    Article  CAS  Google Scholar 

  55. S. Trofimenko, J. Chem. Educ. 82, 1715 (2005)

    Article  CAS  Google Scholar 

  56. N. Burzlaff, Angew. Chem. Int. Ed. 48, 5580 (2009)

    Article  CAS  Google Scholar 

  57. S. Trofimenko, J. Am. Chem. Soc. 88, 1842 (1966)

    Article  CAS  Google Scholar 

  58. S. Trofimenko, Prog. Inorg. Chem. 34, 115 (1986)

    Article  CAS  Google Scholar 

  59. S. Trofimenko, Chem. Rev. 93, 943 (1993)

    Article  CAS  Google Scholar 

  60. N. Kitajima, Y. Moro-oka, Chem. Rev. 94, 737 (1994)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  62. D.L. Reger, C.A. Little, A.L. Rheingold, R. Sommer, G.J. Long, Inorg. Chim. Acta 316, 65 (2001)

    Article  CAS  Google Scholar 

  63. H. Pfeiffer, A. Rojas, J. Niesel, U. Schatzschneider, Dalton Trans. (22), 4292 (2009)

    Google Scholar 

  64. R.R. Schrock, D.V. Yandulov, Science 301, 76 (2003)

    Article  Google Scholar 

  65. R.A. Kinney, D.G.H. Hetterscheid, B.S. Hanna, R.R. Schrock, B.M. Hoffman, Inorg. Chem. 49, 704 (2009)

    Article  Google Scholar 

  66. M.R. Reithofer, R.R. Schrock, P. Müller, J. Am. Chem. Soc. 132, 8349 (2010)

    Article  CAS  Google Scholar 

  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. C.E. MacBeth, A.P. Golombek, V.G. Young Jr., C. Yang, K. Kuczera, M.P. Hendrich, A.S. Borovik, Science 289, 938 (2000)

    Article  CAS  Google Scholar 

  69. D.M. Jenkins, T.A. Betley, J.C. Peters, J. Am. Chem. Soc. 124, 11238 (2002)

    Article  CAS  Google Scholar 

  70. T.A. Betley, J.C. Peters, J. Am. Chem. Soc. 126, 6252 (2004)

    Article  CAS  Google Scholar 

  71. S.D. Brown, T.A. Betley, J.C. Peters, J. Am. Chem. Soc. 125, 322 (2003)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  73. H.V.R. Dias, W.C. Jin, Tetrahedron Lett. 35, 1365 (1994)

    Article  CAS  Google Scholar 

  74. H. Nakai, Y. Tang, P. Gantzel, K. Meyer, Chem. Commun. (1), 24 (2003)

    Google Scholar 

  75. U. Kernbach, M. Ramm, P. Luger, W.P. Fehlhammer, Angew. Chem. Int. Ed. 35, 310 (1996)

    Article  CAS  Google Scholar 

  76. R. Fränkel, C. Birg, U. Kernbach, T. Habereder, H. Nöth, W.P. Fehlhammer, Angew. Chem. Int. Ed. 40, 1907 (2001)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  78. J.J. Scepaniak, J.A. Young, R.P. Bontchev, J.M. Smith, Angew. Chem. Int. Ed. 48, 3158 (2009)

    Google Scholar 

  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)

    Article  CAS  Google Scholar 

  80. K. Chen, M. Costas, J. Kim, A.K. Tipton, L. Que, J. Am. Chem. Soc. 124, 3026 (2002)

    Article  CAS  Google Scholar 

  81. M. Costas, M.P. Mehn, M.P. Jensen, L. Que Jr., Chem. Rev. 104, 939 (2004)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  83. K. Meyer, E. Bill, B. Mienert, T. Weyhermüller, K. Wieghardt, J. Am. Chem. Soc. 121, 4859 (1999)

    Article  CAS  Google Scholar 

  84. M. Aliaga-Alcalde, S.D. George, B. Mienert, E. Bill, K. Wieghardt, F. Neese, Angew. Chem. Int. Ed. 44, 2908 (2005)

    Article  CAS  Google Scholar 

  85. C.A. Grapperhaus, B. Mienert, E. Bill, T. Weyhermüller, K. Wieghardt, Inorg. Chem. 39, 5306 (2000)

    Article  CAS  Google Scholar 

  86. J.F. Berry, E. Bill, E. Bothe, S.D. George, B. Mienert, F. Neese, K. Wieghardt, Science 312, 1937 (2006)

    Article  CAS  Google Scholar 

  87. G. Ertl, Chem. Rec. 1, 33 (2001)

    Article  CAS  Google Scholar 

  88. B.M. Hoffman, D.R. Dean, L.C. Seefeldt, Acc. Chem. Res. 42, 609 (2009)

    Article  CAS  Google Scholar 

  89. G. Ertl, Angew. Chem. Int. Ed. 29, 1219 (1990)

    Article  Google Scholar 

  90. O. Einsle, F.A. Tezcan, S.L.A. Andrade, B. Schmid, M. Yoshida, J.B. Howard, D.C. Rees, Science 297, 1696 (2002)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  93. D.S. Scholl, J.A. Steckel, Density Functional Theory: A Practical Introduction (Wiley, Hoboken, 2009)

    Book  Google Scholar 

  94. K. Meyer, J. Bendix, N. Metzler-Nolte, T. Weyhermüller, K. Wieghardt, J. Am. Chem. Soc. 120, 7260 (1998)

    Article  CAS  Google Scholar 

  95. C.J. Ballhausen, H.B. Gray, Inorg. Chem. 1, 111 (1962)

    Article  CAS  Google Scholar 

  96. J.R. Winkler, H.B. Gray, J. Am. Chem. Soc. 105, 1373 (1983)

    Article  CAS  Google Scholar 

  97. J.R. Winkler, H.B. Gray, Inorg. Chem. 24, 346 (1985)

    Article  CAS  Google Scholar 

  98. J. Bendix, J. Am. Chem. Soc. 125, 13348 (2003)

    Article  CAS  Google Scholar 

  99. K. Meyer, J. Bendix, E. Bill, T. Weyhermüller, K. Wieghardt, Inorg. Chem. 37, 5180 (1998)

    Article  CAS  Google Scholar 

  100. A. Niemann, U. Bossek, G. Haselhorst, K. Wieghardt, B. Nuber, Inorg. Chem. 35, 906 (1996)

    Article  CAS  Google Scholar 

  101. J. Bendix, K. Meyer, T. Weyhermüller, E. Bill, N. Metzler-Nolte, K. Wieghardt, Inorg. Chem. 37, 1767 (1998)

    Article  CAS  Google Scholar 

  102. J. Bendix, R.J. Deeth, T. Weyhermüller, E. Bill, K. Wieghardt, Inorg. Chem. 39, 930 (2000)

    Article  CAS  Google Scholar 

  103. M. Aliaga-Alcalde, S.D. George, B. Mienert, E. Bill, K. Wieghardt, F. Neese, Angew. Chem. Int. Ed. 44, 2908 (2005)

    Article  CAS  Google Scholar 

  104. T.A. Betley, J.C. Peters, J. Am. Chem. Soc. 125, 10782 (2003)

    Article  CAS  Google Scholar 

  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. C.M. Thomas, N.P. Mankad, J.C. Peters, J. Am. Chem. Soc. 128, 4956 (2006)

    Article  CAS  Google Scholar 

  107. C.M. Thomas, J.C. Peters, Angew. Chem. Int. Ed. 45, 776 (2006)

    Article  CAS  Google Scholar 

  108. X. Hu, K. Meyer, J. Am. Chem. Soc. 126, 16322 (2004)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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. 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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry and Pharmacy, Inorganic Chemistry, Friedrich-Alexander-University Erlangen-Nuremberg, Egerlandstraße 1, 91058, Erlangen, Germany

    Carola S. Vogel

Authors
  1. Carola S. Vogel
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Carola S. Vogel .

Rights and permissions

Reprints and permissions

Copyright information

© 2012 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Vogel, C.S. (2012). Introduction to Tripodal N-Heterocyclic Carbene Iron Complexes. In: High- and Low-Valent tris-N-Heterocyclic Carbene Iron Complexes. Springer Theses. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-27254-7_1

Download citation

Publish with us

Policies and ethics

Search

Navigation