Skip to main content
SpringerLink
Log in

N-Heterocyclic Carbenes in Catalysis—An Introduction

  • Chapter
  • First Online:
Topics in Organometallic Chemistry

Part of the book series: Topics in Organometallic Chemistry

Abstract

N-Heterocyclic carbene (NHC) has become a major ligand class and has proven to be more than just a “phosphine mimic”. Some important features like electronic and steric properties are discussed and typical examples of NHC are given herein.

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

Access this chapter

Log in via an institution

Institutional subscriptions

References

  1. Bertrand G (2002) Carbene Chemistry. Marcel Dekker, New York

    Google Scholar 

  2. Herrmann WA, Köcher C (1997) Angew Chem Int Ed 36:2162

    CAS  Google Scholar 

  3. Wanzlick HW (1962) Angew Chem Int Ed Engl 1:75

    Google Scholar 

  4. Wanzlick H-W, Schönherr H-J (1968) Angew Chem Int Ed Engl 7:141

    CAS  Google Scholar 

  5. Öfele K (1968) J Organomet Chem 12:P42

    Google Scholar 

  6. Arduengo III AJ, Harlow RL, Kline M (1991) J Am Chem Soc 113:361

    CAS  Google Scholar 

  7. Arduengo III AJ, Krafczyk R (1998) Chem Unserer Zeit 32:6

    CAS  Google Scholar 

  8. Kirmse W (2004) Angew Chem Int Ed 43:1767

    CAS  Google Scholar 

  9. Bourissou D, Guerret O, Gabbaï FP, Bertrand G (2000) Chem Rev 100:39

    PubMed  CAS  Google Scholar 

  10. Hahn FE (2006) Angew Chem Int Ed 45:1348

    CAS  Google Scholar 

  11. Herrmann WA, Elison M, Fischer J, Köcher C, Arthus GR (1995) Angew Chem Int Ed 34:2371

    CAS  Google Scholar 

  12. Herrmann WA (2002) Angew Chem Int Ed 41:1291

    Google Scholar 

  13. Enders D, Balensiefer T (2004) Acc Chem Res 37:534

    PubMed  CAS  Google Scholar 

  14. Grasa GA, Singh R, Nolan SP (2004) Synthesis, 971

    Google Scholar 

  15. Johnson JS (2004) Angew Chem Int Ed 43:1326

    CAS  Google Scholar 

  16. Christmann M (2005) Angew Chem Int Ed 44:2632

    CAS  Google Scholar 

  17. Zeitler K (2005) Angew Chem Int Ed 44:7506

    CAS  Google Scholar 

  18. Termaten AT, Schakel M, Ehlers AW, Lutz M, Spek AL, Lammertsma K (2003) Chem Eur J 9:3577

    CAS  Google Scholar 

  19. Lee MT, Hu CH (2004) Organometallics 23:976

    CAS  Google Scholar 

  20. Hu XL, Castro-Rodriguez I, Meyer K (2004) J Am Chem Soc 126:13464

    PubMed  CAS  Google Scholar 

  21. Cavallo L, Correa A, Costabile C, Jacobsen H (2005) J Organomet Chem 690:5407

    CAS  Google Scholar 

  22. Chianese AR, Li X, Janzen MC, Faller JW, Crabtree RH (2003) Organometallics 22:1663

    CAS  Google Scholar 

  23. Dorta R, Stevens ED, Scott NM, Costabile C, Cavallo L, Hoff CD, Nolan SP (2005) J Am Chem Soc 127:2485

    PubMed  CAS  Google Scholar 

  24. Crabtree RH (2005) J Organomet Chem 690:5451

    CAS  Google Scholar 

  25. Perrin L, Clot E, Eisenstein O, Loch J, Crabtree RH (2001) Inorg Chem 40:5806

    PubMed  CAS  Google Scholar 

  26. Tolman CA (1977) Chem Rev 77:313

    CAS  Google Scholar 

  27. Nonnenmacher M, Kunz D, Rominger F, Oeser T (2006) Chem Commun, 1378

    Google Scholar 

  28. Littke AF, Fu GC (2002) Angew Chem Int Ed 41:4176

    CAS  Google Scholar 

  29. Dorta R, Stevens ED, Hoff CD, Nolan SP (2003) J Am Chem Soc 125:10490

    PubMed  CAS  Google Scholar 

  30. Becker E, Stingl V, Dazinger G, Puchberger M, Mereiter K, Kirchner K (2006) J Am Chem Soc 128:6572

    PubMed  CAS  Google Scholar 

  31. Galan BR, Gembicky M, Dominiak PM, Keister JB, Diver ST (2005) J Am Chem Soc 127:15702

    PubMed  CAS  Google Scholar 

  32. Allen DP, Crudden CM, Calhoun LA, Wang RY (2004) J Organomet Chem 689:3203

    CAS  Google Scholar 

  33. Dorta R, Stevens ED, Hoff CD, Nolan SP (2003) J Am Chem Soc 125:10490

    PubMed  CAS  Google Scholar 

  34. Danopoulos AA, Tsoureas N, Green JC, Hursthouse MB (2003) Chem Commun, 756

    Google Scholar 

  35. Jazzar RFR, Macgregor SA, Mahon MF, Richards SP, Whittlesey MK (2002) J Am Chem Soc 124:4944

    PubMed  CAS  Google Scholar 

  36. Simms RW, DrewittMJ, Baird M (2002) Organometallics 21:2958

    CAS  Google Scholar 

  37. McGuiness DS, Saendig N, Yates BF, Cavell KJ (2001) J Am Chem Soc 123:4029

    Google Scholar 

  38. Titcomb LR, Caddick S, Cloke FGN, Wilson DJ, McKerrecher (2001) Chem Commun, 1388

    Google Scholar 

  39. Huang J, Schanz H-J, Stevens ED, Nolan SP (1999) Organometallics 18:2370

    CAS  Google Scholar 

  40. Hillier AC, Sommer WJ, Yong BS, Petersen JL, Cavallo L, Nolan SP (2003) Organometallics 22:4322

    CAS  Google Scholar 

  41. Amyes TL, Diver ST, Richard JP, Rivas FM, Toth K (2004) J Am Chem Soc 126:4366

    PubMed  CAS  Google Scholar 

  42. Chen H, Justes DR, Cooks RG (2005) Org Lett 7:3949

    PubMed  CAS  Google Scholar 

  43. Grimmet MR (1997) Imidazole and Benzimidazole Synthesis. Academic Press, San Diego

    Google Scholar 

  44. Arduengo III AJ, Krafczyk R, Schmutzler R (1999) Tetrahedron 55:14523

    CAS  Google Scholar 

  45. Herrmann WA, Köcher C, Gooßen LJ, Artus GRJ (1996) Chem Eur J 2:1627

    CAS  Google Scholar 

  46. Arduengo III AJ, Dias HVR, Harlow RL, Kline M (1992) J Am Chem Soc 114:5530

    CAS  Google Scholar 

  47. Glorius F, Altenhoff G, Goddard R, Lehmann C (2002) Chem Commun, 2704

    Google Scholar 

  48. Wang A-E, Xie J-H, Wang L-X, Zhou Q-L (2005) Tetrahedron 61:259

    CAS  Google Scholar 

  49. Perry MC, Cui X, Powell MT, Hou D-R, Reibenspies JH, Burgess K (2003) J Am Chem Soc 125:113

    PubMed  CAS  Google Scholar 

  50. César V, Bellemin-Laponnaz S, Gade LH (2002) Organometallics 21:5204

    Google Scholar 

  51. Loch JA, Albrecht M, Peris E, Mata J, Faller JW, Crabtree RH (2002) Organometallics 21:700

    CAS  Google Scholar 

  52. Yang C, Lee HM, Nolan SP (2001) Org Lett 3:1511

    PubMed  CAS  Google Scholar 

  53. Gardiner MG, Herrmann WA, Reisinger C-P, Schwarz J, Spiegler M (1999) J Organomet Chem 572:239

    CAS  Google Scholar 

  54. Herrmann WA, Gooßen LJ, Spiegler M (1998) Organometallics 17:2162

    CAS  Google Scholar 

  55. Herrmann WA, Gooßen LJ, Spiegler M (1997) J Organomet Chem 547:357

    CAS  Google Scholar 

  56. Hadei N, Kantchev EAB, O'Brien CJ, Organ MG (2005) J Org Chem 70:8503

    PubMed  CAS  Google Scholar 

  57. Waltman AW, Grubbs RH (2004) Organometallics 23:3105

    CAS  Google Scholar 

  58. Despagnet-Ayoub E, Grubbs RH (2004) J Am Chem Soc 126:10198

    PubMed  CAS  Google Scholar 

  59. Despagnet-Ayoub E, Grubbs RH (2005) Organometallics 24:338

    CAS  Google Scholar 

  60. Altenhoff G, Goddard R, Lehmann CW, Glorius F (2003) Angew Chem Int Ed 42:3690

    CAS  Google Scholar 

  61. Altenhoff G, Goddard R, Lehmann CW, Glorius F (2004) J Am Chem Soc 126:15195

    PubMed  CAS  Google Scholar 

  62. Burstein C, Lehmann CW, Glorius F (2005) Tetrahedron 61:6207

    CAS  Google Scholar 

  63. Alcarazo M, Roseblade SJ, Cowley AR, Fernandez R, Brown JM, Lassaletta JM (2005) J Am Chem Soc 127:3290

    PubMed  CAS  Google Scholar 

  64. Lavallo V, Canac Y, Präsang C, Donnadieu B, Bertrand G (2005) Angew Chem Int Ed 44:5705

    CAS  Google Scholar 

  65. Lavallo V, Canac Y, DeHope A, Donnadieu B, Bertrand G (2005) Angew Chem Int Ed 44:7236

    CAS  Google Scholar 

  66. Yamashita M, Goto K, Kawashima T (2005) J Am Chem Soc 127:7294

    PubMed  CAS  Google Scholar 

  67. Altenhoff G, Würtz S, Glorius F (2006) Tetrahedron Lett 47:2925

    CAS  Google Scholar 

  68. Raubenheimer HG, Lindeque L, Cronje S (1996) J Organomet Chem 511:177

    CAS  Google Scholar 

  69. Köcher C, Herrmann WA (1997) J Organomet Chem 532:261

    Google Scholar 

  70. Hahn FE, Wittenbecher L, Boese R, Blaser D (1999) Chem Eur J 5:1931

    CAS  Google Scholar 

  71. Hahn FE, Wittenbecher L, Le Van D, Fröhlich R (2000) Angew Chem Int Ed 39:541

    CAS  Google Scholar 

  72. Tan KL, Bergman RG, Ellman JA (2002) J Am Chem Soc 124:3202

    PubMed  CAS  Google Scholar 

  73. Metallinos C, Barrett FB, Chaytor JL, Heska MEA (2004) Org Lett 6:3641

    PubMed  CAS  Google Scholar 

  74. Hadei N, Kantchev EAB, O'Brien CJ, Organ MG (2005) Org Lett 7:1991

    PubMed  CAS  Google Scholar 

  75. O'Brien CJ, Kantchev EAB, Chass GA, Hadei N, Hopkinson AC, Organ MG, Setiadi DH, Tang T-H, Fang D-C (2005) Tetrahedron 61:9723

    Google Scholar 

  76. Weiss R, Reichel S, Handke M, Hampel F (1998) Angew Chem Int Ed 37:344

    CAS  Google Scholar 

  77. Weiss R, Reichel S (2000) Eur J Inorg Chem 1935

    Google Scholar 

  78. Nonnenmacher M, Kunz D, Rominger F, Oeser T (2005) J Organomet Chem 690:5647

    CAS  Google Scholar 

  79. Lebel H, Janes MK, Charette AB, Nolan SP (2004) J Am Chem Soc 126:5046

    PubMed  CAS  Google Scholar 

  80. Gründemann S, Kovacevic A, Albrecht M, Faller JW, Crabtree RH (2002) J Am Chem Soc 124:10473

    PubMed  Google Scholar 

  81. Gründemann S, Kovacevic A, Albrecht M, Faller JW, Crabtree RH (2001) Chem Commun, 2274

    Google Scholar 

  82. Sole S, Gornitzka H, Schoeller WW, Bourisou D, Bertrand G (2001) Science 292:1901

    PubMed  CAS  ADS  Google Scholar 

  83. Cattoen X, Gornitzka H, Bourissou D, Bertrand G (2004) J Am Chem Soc 126:1342

    PubMed  Google Scholar 

  84. Lavallo V, Mafhouz J, Canac Y, Donnadieu B, Schoeller WW, Bertrand G (2004) J Am Chem Soc 126:8670

    PubMed  CAS  Google Scholar 

  85. Krahulic KE, Enright GD, Parvez M, Roesler R (2005) J Am Chem Soc 127:4142

    PubMed  CAS  Google Scholar 

  86. Enders D, Breuer K, Raabe G, Runsink J, Teles JH, Melder J-P, Ebel K, Brode S (1995) Angew Chem Int Ed Engl 34:1021

    CAS  Google Scholar 

  87. Ruiz J, Garciá G, Mosquera MEG, Perandones BF, Gonzalo MP, Vivanco M (2005) J Am Chem Soc 127:8584

    PubMed  CAS  Google Scholar 

  88. Tamm M, Hahn FE (1999) Coord Chem Rev 182:175

    Google Scholar 

  89. Basato M, Michelin RA, Mozzon M, Sgarbossa P, Tassan A (2005) J Organomet Chem 690:5414

    CAS  Google Scholar 

  90. Arduengo III AJ, Goerlich JR, Marshall WJ (1997) Liebigs Ann, p 365

    Google Scholar 

  91. Alder RW, Blake ME, Chaker L, Harvey JN, Paolini F, Schütz J (2004) Angew Chem Int Ed 43:5896

    CAS  Google Scholar 

  92. Alder RW, Blake ME, Bortolotti C, Bufali S, Butts CP, Linehan E, Oliva JM, Orpen AG, Quayle MJ (1999) Chem Commun, 241

    Google Scholar 

  93. Guillen F, Winn CL, Alexakis A (2001) Tetrahedron: Asymmetry 12:2083

    CAS  Google Scholar 

  94. Mayr M, Wurst K, Ongania K-H, Buchmeiser MR (2004) Chem Eur J 10:1256

    CAS  Google Scholar 

  95. Yun J, Marinez ER, Grubbs RH (2004) Organometallics 23:4172

    CAS  Google Scholar 

  96. Bazinet P, Yap GPA, Richeson DS (2003) J Am Chem Soc 125:13314

    PubMed  CAS  Google Scholar 

  97. Präsang C, Donnadieu B, Bertrand G (2005) J Am Chem Soc 127:10182

    PubMed  Google Scholar 

  98. Scarborough CC, Grady MJW, Guzei IA, Gandhi BA, Bunel EE, Stahl SS (2005) Angew Chem Int Ed 44:5269

    CAS  Google Scholar 

  99. Yun J, Marinez ER, Grubbs RH (2004) Organometallics 23:4172

    CAS  Google Scholar 

  100. Mayr M, Wurst K, Ongania K-H, Buchmeiser MR (2004) Chem Eur J 10:1256

    CAS  Google Scholar 

  101. Kastrup CJ, Oldfield SV, Rzepa HS (2002) J Chem Soc Dalton Trans, p 2421

    Google Scholar 

  102. Kastrup CJ, Oldfield SV, Rzepa HS (2002) Chem Commun, 642

    Google Scholar 

  103. Frey GD, Schütz J, Herdtweck E, Herrmann WA (2005) Organometallics 24:4416

    CAS  Google Scholar 

  104. Viciu MS, Kelly RA, Stevens ED, Naud F, Studer M, Nolan SP (2003) Org Lett 5:1479

    PubMed  CAS  Google Scholar 

  105. Navarro O, Marion N, Scott NM, Gonzalez J, Amoroso D, Bell A, Nolan SP (2005) Tetrahedron 61:9716

    CAS  Google Scholar 

  106. Marion N, Navarro O, Mei J, Stevens ED, Scott NM, Nolan SP (2006) J Am Chem Soc 128:4101

    PubMed  CAS  Google Scholar 

  107. Navarro O, Nolan SP (2006) Synthesis, 366

    Google Scholar 

  108. O'Brien CJ, Kantchev EAB, Valente C, Hadei N, Chass GA, Lough A, Hopkinson AC, Organ MG (2006) Chem Eur J 12:4743

    Google Scholar 

  109. Organ MG, Avola S, Dubovyk I, Hadei N, Kantchev EAB, O'Brien CJ, Valente C (2006) Chem Eur J 12:4749

    CAS  Google Scholar 

  110. Boydston AJ, Williams KA, Bielawaski CW (2005) J Am Chem Soc 127:12496

    PubMed  CAS  Google Scholar 

  111. Muelhofer M, Strassner T, Herrmann WA (2002) Angew Chem Int Ed 41:1745

    Google Scholar 

  112. Kernbach U, Ramm M, Luger P, Fehlhammer WP (1996) Angew Chem Int Ed Engl 35:310

    CAS  Google Scholar 

  113. Fränkel R, Kernbach U, Bakola-Christianopoulou M, Plaia U, Suter M, Ponikwar W, Nöth H, Moinet C, Fehlhammer WP (2001) J Organomet Chem 530:617–618

    Google Scholar 

  114. Hahn FE, García Plumed C, Münder M, Lügger T (2004) Chem Eur J 10:6285

    CAS  Google Scholar 

  115. Hahn FE, Langenhahn V, Lügger T, Pape T, Le Van D (2005) Angew Chem Int Ed 44:3759

    CAS  Google Scholar 

  116. Hahn FE, Langenhahn V, Pape T (2005) Chem Commun, 5390

    Google Scholar 

Download references

Acknowledgments

I thank the Fond der Chemischen Industrie and the Deutsche Forschungsgemeinschaft for generous support of my work.

Author information

Authors and Affiliations

  1. Fachbereich Chemie, Philipps-Universität, Hans-Meerwein-Straße, 35032, Marburg, Germany

    Frank Glorius

Authors
  1. Frank Glorius
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Frank Glorius .

Rights and permissions

Reprints and permissions

Copyright information

© 2006 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Glorius, F. (2006). N-Heterocyclic Carbenes in Catalysis—An Introduction. In: Topics in Organometallic Chemistry. Springer, . https://doi.org/10.1007/3418_2006_059

Download citation

  • DOI: https://doi.org/10.1007/3418_2006_059

  • Published:

  • Publisher Name: Springer,

Publish with us

Policies and ethics

Search

Navigation