Skip to main content
SpringerLink
Log in

N-Heterocyclic Carbene Complexes in Arylation Reactions other than Cross-couplings

  • Chapter
  • First Online:
N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 32))

  • 1982 Accesses

Abstract

This chapter highlights the use of N-heterocyclic carbenes as supporting ligands in arylation reactions different than the more common cross-coupling reactions, including C-F bond activation, catalytic arylation, homocoupling, direct arylation and oxidative Heck reactions.

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 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
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. (a) de Meijere A, Diederich F (2004) Metal-catalysed cross-coupling reactions. Wiley-VCH, Weinheim; (b) Beller M, Bolm C (2004) Transition metals for organic synthesis. Wiley-VCH, Weinheim

    Google Scholar 

  2. Ackermann L (2009) Modern arylation methods. Wiley-VCH, Weinheim

    Book  Google Scholar 

  3. (a) Hermann WA (2002) Angew Chem Int Ed 41:1290–1309; (b) Nolan SP (2006) N-heterocyclic carbenes in synthesis. Wiley-VCH: Weinheim; (c) Glorius F (2007) N-heterocyclic carbenes in transition metal catalysis. Springer-Verlag, Berlin; (d) Díez-González S, Nolan SP (2007) Coord Chem Rev 251:874–883

    Google Scholar 

  4. (a) Hiyama T (2000) Organofluorine Compounds. Springer-Verlag, Berlin; (b) Chambers RD (2004) Fluorine in organic chemistry. Blackwell, Oxford ; (c) Kirsch P (2004) Modern fluoroorganic chemistry: synthesis, reactivity, applications. Wiley-VCH, Weinheim (d) Uneyama K (2006) Organofluorine chemistry. Blackwell, Oxford

    Google Scholar 

  5. (a) Lemal DM (2004) J Org Chem 69:1–11 (b) O’Hagan D (2008) Chem Soc Rev 37:308–319

    Google Scholar 

  6. Blanksby SJ, Ellison GB (2003) Acc Chem Res 36:255–263

    Article  CAS  Google Scholar 

  7. (a) Kiplinger JL, Richmond TG, Osterberg CE (1994) Chem Rev 94:373–431 ; (b) Burdeniuc J, Jedlicka B, Crabtree RH (1997) Chem Ber/Recueil 130:145–154 ; (c) Amii H, Uneyama K (2009) Chem Rev 109:2119–2183

    Google Scholar 

  8. Torrens H (2005) Coord Chem Rev 249:1957–1985

    Article  CAS  Google Scholar 

  9. Braun T, Perutz RN (2002) Chem Commun 2749–2757

    Google Scholar 

  10. Whittlesey MK, Perutz RN, Moore MH (1996) Chem Commun 787–788

    Google Scholar 

  11. Fahey DR, Mahan JE (1977) J Am Chem Soc 99:2501–2508

    Article  CAS  Google Scholar 

  12. Cronin L, Higgitt CL, Karch R, Perutz RN (1997) Organometallics 16:4920–4928

    Article  CAS  Google Scholar 

  13. Schaub T, Radius U (2005) Chem Eur J 11:5024–5030

    Article  CAS  Google Scholar 

  14. Schaub T, Backes M, Radius U (2008) Eur J Inorg Chem 2680–2690

    Google Scholar 

  15. Schaub T, Fischer P, Steffen A, Braun T, Radius U, Mix A (2008) J Am Chem Soc 130:9304–9317

    Article  CAS  Google Scholar 

  16. Jasim NA, Perutz RN, Whitwood AC, Braun T, Izundu J, Neumann B, Rothfeld S, Stammler H-G (2004) Organometallics 23:6140–6149

    Article  CAS  Google Scholar 

  17. Reade SP, Acton AL, Mahon MF, Martin TA, Whittlesey MK (2009) Eur J Inorg Chem 1774–1785

    Google Scholar 

  18. Schmidt F, Stemnler RT, Rudolph J, Bolm C (2006) Chem Soc Rev 35:454–470

    CAS  Google Scholar 

  19. Fagnou K, Lautens M (2003) Chem Rev 103:169–196

    Article  CAS  Google Scholar 

  20. (a) Sakai M, Ueda M, Miyaura N (1998) Angew Chem Int Ed 37:3279–3281 (b) Ueda M, Miyaura N (2000) J Org Chem 65:4450–4452

    Google Scholar 

  21. Fürstner A, Krause H (2001) Adv Synth Catal 343:343–350

    Article  Google Scholar 

  22. Díez-González S, Marion N, Nolan SP (2009) Chem Rev 109:3612–3676

    Article  Google Scholar 

  23. (a) Imlinger N, Mayr M, Wang D, Wurst K, Buchmeiser MR (2004) Adv Synth Catal 346:1836–1843 ; (b) Imlinger N, Wurst K, Buchmeiser MR (2005) J Organomet Chem 690:4433–4440

    Google Scholar 

  24. (a) Özdemir I, Demir S, Çetinkaya B (2004) J Mol Catal A: Chem 215:45–48 ; (b) Yiğit M, Özdemir I, Çetinkaya E, Çetinkaya B (2005) Heteroat Chem 16:461–465 ; (c) Kilinçarslan R, Yiğit M, Özdemir I, Çetinkaya E, Çetinkaya B (2007) J Heterocycl Chem 44:69–73 ; (d) Özdemir I, Yiğit M, Çetinkaya E, Çetinkaya B (2006) Heterocycles 68:1371–1379 ; (e) Yiğit M, Özdemir I (2007) Transition Met Chem 32:536–540

    Google Scholar 

  25. Özdemir I, Demir S, Çetinkaya B, Çetinkaya E (2005) J Organomet Chem 690:5849–5855

    Article  Google Scholar 

  26. Özdemir I, Gürbüz N, Gök Y (2005) Transition Met Chem 30:367–371

    Article  Google Scholar 

  27. (a) Gois PMP, Trindade AF, Veiros LF, André V, Duarte MT, Afonso CAM, Caddick S, Cloke FGN (2007) Angew Chem Int Ed 46:5750–5753 ; (b) Trindade AF, Gois PMP, Veiros LF, André V, Duarte MT, Afonso CAM, Caddick S, Cloke FGN (2008) J Org Chem 73:4076–4086

    Google Scholar 

  28. (a) Özdemir I, Gürbüz N, Seçkin T, Çetinkaya B (2005) Appl Organometal Chem 19:633–638; (b) Yan C, Zeng X, Zhang W, Luo M (2006) J Organomet Chem 691:3391–3396

    Google Scholar 

  29. Williams L, Zhang Z, Shao F, Carroll PJ, Joullié MM (1996) Tetrahedron 52:11673–11674

    Article  CAS  Google Scholar 

  30. Zhang W, Qin Y, Zhang S, Luo M (2005) Arkivoc 14:39–48

    Article  CAS  Google Scholar 

  31. Arao T, Sato K, Kondo K, Aoyama T (2006) Chem Pharm Bull 54:1576–1581

    Article  CAS  Google Scholar 

  32. Focken T, Rudolph J, Bolm C (2005) Synlett 429–436

    Google Scholar 

  33. Kuriyama M, Shimazawa R, Shirai R (2008) J Org Chem 73:1597–1600

    Article  CAS  Google Scholar 

  34. Kuriyama M, Shimazawa R, Enomoto T, Shirai R (2008) J Org Chem 73:6939–6942

    Article  CAS  Google Scholar 

  35. Bouffard J, Itami K (2009) Org Lett 11:4410–4413

    Article  CAS  Google Scholar 

  36. Legault CY, Kendall C, Charette AB (2005) Chem Commun 3826–3828

    Google Scholar 

  37. Bakar Md A, Suzuki Y, Sato M (2008) Chem Pharm Bull 56:973–976

    Article  Google Scholar 

  38. Ma G-N, Zhang T, Shi M (2009) Org Lett 11:875–878

    Article  CAS  Google Scholar 

  39. Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M (2002) Chem Rev 102:1359–1469

    Article  CAS  Google Scholar 

  40. Stanforth SP (1998) Tetrahedron 54:263–303

    Article  CAS  Google Scholar 

  41. Ullmann F, Bielecki J (1901) Chem Ber 34:2174–2185

    Article  CAS  Google Scholar 

  42. For recent reviews of cross–coupling reactions with copper–based catalyst, see: (a) Lindley J (1984) Tetrahedron 40:1433–1456 ; (b) Ley SV, Thomas AW (2003) Angew Chem Int Ed 42:5400–5449 ; (c) Kunz K, Scholz U, Ganzer D (2003) Synlett 2428–2439 ; (d) Beletskaya IP, Cheprakov AV (2004) Coord Chem Rev 248:2337–2364

    Google Scholar 

  43. de Meijere A, Diederich F (2004) Metal-catalysed cross-coupling reactions, 2nd edn, vols 1 and 2. Wiley-VCH, Weinheim

    Google Scholar 

  44. (a) Miyaura N, Yamada K, Suzuki A (1979) Tetrahedron Lett 36:3437–3440; (b) Miyaura N, Suzuki A (1995) Chem Rev 95:2457–2483; (c) Kotha S, Lahiri K, Kashinath D (2002) Tetrahedron 58:9633–9695

    Google Scholar 

  45. Nelson TD, Crouch RD (2004) Org React 63:265–555

    CAS  Google Scholar 

  46. Smith KA, Campi EM, Jackson WR, Marcuccio S, Naeslund CGM, Deacon GB (1997) Synlett 131–132

    Google Scholar 

  47. Wong MS, Zhang XL (2001) Tetrahedron Lett 42:4087–4089

    Article  CAS  Google Scholar 

  48. (a) O’Keefe DF, Dannock MC, Marcuccio SM (1992) Tetrahedron Lett 33:6679–6680; (b) Goodson FE, Wallow TI, Novak BM (1997) J Am Chem Soc 119:12441–12453

    Google Scholar 

  49. Yamamoto Y, Suzuki R, Hattori K, Nishiyama H (2006) Synlett 1027–1030

    Article  Google Scholar 

  50. Yamamoto Y (2007) Synlett 1913–1916

    Article  Google Scholar 

  51. Jin Z, Guo S-X, Gu X-P, Qiu L-L, Song H-B, Fang J-X (2009) Adv Synth Catal 351:1575–1585

    Article  CAS  Google Scholar 

  52. (a) Alberico D, Scott ME, Lautens M (2007) Chem Rev 107:174–238 ; (b) McGlacken GP, Bateman LM (2009) Chem Soc Rev 38:2447–2464

    Google Scholar 

  53. (a) Özdemir I, Demir S, Çetinkaya B, Gourlaouen C, Maseras F, Bruneau C, Dixneuf PH (2008) J Am Chem Soc 130:1156–1157; (b) Özdemir I, Demir S, Gürbüz N, Çetinkaya B, Toupet L, Bruneau C, Dixneuf PH (2009) Eur J Inorg Chem 1942–1949

    Google Scholar 

  54. (a) Gürbüz N, Özdemir I, Çetinkaya B (2005) Tetrahedron Lett 46:2273–2277 ; (b) Doğan Ö, Gürbüz N, Özdemir I, Çetinkaya B (2009) J Heterocyclic Chem 46:186–190

    Google Scholar 

  55. Ho C-C, Chatterjee S, Wu T-L, Chan K-T, Chang Y-W, Hsiao T-H, Lee HM (2009) Organometallics 28:2837–2847

    Article  CAS  Google Scholar 

  56. Campeau L-C, Parisien M, Leblanc M, Fagnou K (2004) J Am Chem Soc 126:9186–9187

    Article  CAS  Google Scholar 

  57. Campeau L-C, Thansandote P, Fagnou K (2005) Org Lett 7:1857–1860

    Article  CAS  Google Scholar 

  58. (a) Joullie MM, Berritt S, Forbeck EM (2008) Curr Opin Drug Discovery Dev 11:829–852; (b) Nicolaou KC, Chen JS (2008) Pure Appl Chem 80:727–742

    Google Scholar 

  59. Arslan H, Özdemir I, Vanderveer D, Demir S, Çetinkaya B (2009) J Coord Chem 62:2591–2599

    Article  CAS  Google Scholar 

  60. Touré BB, Lane BS, Sames D (2006) Org Lett 8:1979–1982

    Article  Google Scholar 

  61. Deprez NR, Kalyani D, Krause A, Sanford MS (2006) J Am Chem Soc 128:4972–4973

    Article  CAS  Google Scholar 

  62. (a) Mizoroki T, Mori K, Ozaki A (1971) Bull Chem Soc Jpn 44:581 ; (b) Heck RF, Nolley JP Jr (1972) J Org Chem 37:2320–2322 ; (c) de Meijere A, Meyer FE (1994) Angew Chem Int Ed Engl 33:2379–2411

    Google Scholar 

  63. Varseev GN, Maier ME (2006) Angew Chem Int Ed 45:4767–4771

    Article  CAS  Google Scholar 

  64. Stahl SS (2004) Angew Chem Int Ed 43:3400–3420

    Article  CAS  Google Scholar 

  65. (a) Yoo KS, Yoon CH, Jung KW (2006) J Am Chem Soc 128:16384–16393; (b) Enquist P-A, Nilsson P, Sjöberg P, Larhed M (2006) J Org Chem 71:8779–8786

    Google Scholar 

  66. Dieck HA, Heck RF (1975) J Org Chem 40:1083–1090

    Article  CAS  Google Scholar 

  67. Cho CS, Uemura S (1994) J Organomet Chem 465:85–92

    Article  CAS  Google Scholar 

  68. For some recent articles, see: (a) Du X, Suguro M, Hirabayashi K, Mori A (2001) Org Lett 3:3313–3316 ; (b) Andappan MMS, Nilsson P, Larhed M (2003) Mol Diversity 7:97–106 ; (c) Jung YC, Mishra RK, Yoon CH, Jung KW (2003) Org Lett 5:2231–2234 ; (d) Andappan MMS, Nilsson P, Larhed M (2004) Chem Commun 218–219 ; (e) Enquist P-A, Lindh J, Nilsson P, Larhed M (2006) Green Chem 8:338–343 ; (f) Lindh J, Enquist P-A, Pilotti Å, Nilsson P, Larhed M (2007) J Org Chem 72:7957–7962 ; (g) Ruan J, Li X, Saidi O, Xiao J (2008) J Am Chem Soc 130:2424–2425 ; (h) Su Y, Jiao N (2009) Org Lett 11:2980–2983

    Google Scholar 

  69. (a) Akiyama K, Wakabayashi K, Mikami K (2005) Adv Synth Catal 347:1569–1575; (b) Yoo KS, Park CP, Yoon CH, Sakaguchi S, O’Neill J, Jung KW (2007) Org Lett 9:3933–3935 ; (c) Sakaguchi S, Yoo KS, O’Neill J, Lee JH, Stewart T, Jung KW (2008) Angew Chem Int Ed 47:9326–9329

    Google Scholar 

  70. Herrmann WA, Elison M, Fischer J, Köcher C, Artus GRJ (1995) Angew Chem Int Ed 34:2371–2374

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii, 96822, USA

    Oscar Navarro

Authors
  1. Christophe Berini
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Oscar Navarro
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Oscar Navarro .

Editor information

Editors and Affiliations

  1. School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, United Kingdom

    Catherine S.J. Cazin

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer Netherlands

About this chapter

Cite this chapter

Berini, C., Navarro, O. (2010). N-Heterocyclic Carbene Complexes in Arylation Reactions other than Cross-couplings. In: Cazin, C. (eds) N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis. Catalysis by Metal Complexes, vol 32. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-2866-2_7

Download citation

Publish with us

Policies and ethics

Search

Navigation