Skip to main content
Log in

Application of a Nickel-Bispidine Complex as Pre-Catalyst for C(sp 2)–C(sp 3) Bond Formations

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

In the present study, the nickel-catalyzed cross coupling of aryl halides with benzyl zinc bromides or dialkyl zinc reagents to create C(sp 2)–C(sp 3) bonds has been explored. As pre-catalyst the well-defined and easy-accessible (bispidine)Ni(NO3)2 complex has been applied. After investigation of different reaction parameters a broad scope of C(sp 2)–C(sp 3) bond formations were feasible under mild reaction conditions.

Graphical Abstract

.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Fig. 1
Fig. 2
Scheme 5

Similar content being viewed by others

References

  1. Corey EJ, Cheng XM (1989) The logic of chemical synthesis. Wiley, New York, pp 1–91

    Google Scholar 

  2. Suzuki A (2011) Angew Chem 123:6854–6869, Angew Chem Int Ed 2011, 50: 6722–6737

    Google Scholar 

  3. Negishi E (2011) Angew Chem Int Ed 50:6738–6764

    Article  CAS  Google Scholar 

  4. de Meijere F, Diederich (eds) (2004) Metal-catalyzed cross-coupling reactions. Wiley-VCH, Weinheim

  5. Negishi E (ed) (2002) Handbook of organopalladium chemistry for organic synthesis. Wiley-InterScience, New York

    Google Scholar 

  6. Diederich F, Stang PJ (eds) (1998) Metal-catalyzed cross-coupling reactions. Wiley-VCH, Weinhein

    Google Scholar 

  7. Jana R, Pathak TP, Sigman MS (2011) Chem Rev 111:1417–1492

    Article  CAS  Google Scholar 

  8. Hu X (2011) Chem Sci 2:1867–1886

    Article  CAS  Google Scholar 

  9. Rilatt RFW, Jackson J (2008) Org Chem 73:8694–8704

    Article  CAS  Google Scholar 

  10. Zhou S, Fu GC (2003) J Am Chem Soc 125:14726–14727

    Article  CAS  Google Scholar 

  11. Phapale VB, Buñuel E, García-Iglesias M, Cárdenas DJ (2007) Angew Chem Int Ed 46:8790–8795

    Article  CAS  Google Scholar 

  12. Smith SW, Fu GC (2008) Angew Chem 120: 9474–9476, Angew Chem Int Ed 2008, 47:9334–9336

  13. Jones GD, Martin JL, McFarland C, Allen OR, Hall RE, Haley AD, Brandon RJ, Konovalova T, Desrochers PJ, Pulay P, Vicic DA (2006) J Am Chem Soc 128:13175–13183

    Article  CAS  Google Scholar 

  14. Joshi-Pangu A, Ganesh M, Biscoe MR (2011) Org Lett 13:1218–1221

    Article  CAS  Google Scholar 

  15. Comba P, Kanellakopulos B, Katsichtis C, Lienke A, Pritzkow H, Rominger F (1998) J Chem Soc Dalton Trans 23:3997–4001

    Article  Google Scholar 

  16. Börzel H, Comba P, Katsichtis C, Kiefer W, Lienke A, Nagel V, Pritzkow H (1999) Chem Eur J 5:1716–1721

    Article  Google Scholar 

  17. Börzel H, Comba P, Hagen KS, Katsichtis C, Pritzkow H (2000) Chem Eur J 6:914–919

    Article  Google Scholar 

  18. Börzel H, Comba P, Pritzkow H (2001) Chem Commun 97–98

  19. Comba P, Kerscher M, Merz M, Müller V, Pritzkow H, Remenyi R, Schiek W, Xiong Y (2002) Chem Eur J 8:5750–5760

    Article  CAS  Google Scholar 

  20. Börzel H, Comba P, Hagen KS, Kerscher M, Pritzkow H, Schatz M, Schindler S, Walter O (2002) Inorg Chem 41:5440–5452

    Article  Google Scholar 

  21. Börzel H, Comba P, Hagen KS, Lampeka YD, Lienke A, Linti G, Merz M, Pritzkow H, Tsymbal LV (2002) Inorg Chim Acta 337:407–419

    Article  Google Scholar 

  22. Comba P, Hauser A, Kerscher M, Pritzkow H (2003) Angew Chem Int Ed 42:4536–4540

    Article  CAS  Google Scholar 

  23. Comba P, de Laorden CL, Pritzkow H (2005) Helv Chim Acta 88:647–664

    Article  CAS  Google Scholar 

  24. Bautz J, Comba P, Que L Jr (2006) Inorg Chem 45:7077–7082

    Article  CAS  Google Scholar 

  25. Anastasi AE, Lienke A, Comba P, Rohwer H, McGrady JE (2007) Eur J Inorg Chem 65–73

  26. Born K, Comba P, Ferrari R, Lawrance GA, Wadepohl H (2007) Inorg Chem 46:458–464

    Article  CAS  Google Scholar 

  27. Comba P, Kuwata S, Linti G, Tarnai M, Wadepohl H (2007) Eur J Inorg Chem 657–664

  28. Anastasi AE, Comba P, McGrady J, Lienke A, Rohwer H (2007) Inorg Chem 46:6420–6426

    Article  CAS  Google Scholar 

  29. Bentz A, Comba P, Deeth RJ, Kerscher M, Seibold B, Wadepohl H (2008) Inorg Chem 47:9518–9527

    Article  CAS  Google Scholar 

  30. Born K, Comba P, Kerscher M, Linti G, Pritzkow H, Rohwer H (2009) Dalton Trans 362–367

  31. Comba P, Daumann L, Lefebvre J, Linti G, Martin B, Straub J, Zessin T (2009) Aust J Chem 62:1238–1245

    Article  CAS  Google Scholar 

  32. Black DSC, Deacon GB, Rose M (1995) Tetrahedron 51:2055–2076

    Article  CAS  Google Scholar 

  33. Barnes NA, Brooker AT, Godfrey SM, Mallender PR, Pritchard RG, Sadler M (2008) Eur J Org Chem 1019–1030

  34. Walther M, Matterna M, Juran S, Fähnemann S, Stephan H, Kraus W, Emmerling F (2011) Z Naturforsch 66b:721–728

    Article  Google Scholar 

  35. Bleiholder C, Börzel H, Comba P, Ferrari R, Heydt M, Kerscher M, Kuwata S, Laurenczy G, Lawrance GA, Lienke A, Martin B, Merz M, Nuber B, Pritzkow H (2005) Inorg Chem 44:8145–8155

    Article  CAS  Google Scholar 

  36. Comba P, Haaf C, Wadepohl H (2009) Inorg Chem 48:6604–6614

    Article  CAS  Google Scholar 

  37. Atanasov M, Busche C, Comba P, El Hallak F, Martin B, Rajaraman G, van Slageren J, Wadepohl H (2008) Inorg Chem 47:8112–8125

    Article  CAS  Google Scholar 

  38. Comba P, Merz M, Pritzkow H (2003) Eur J Inorg Chem 1711–1718

  39. Born K, Comba P, Daubinet A, Fuchs A, Wadepohl H (2007) J Biol Inorg Chem 12:36–48

    Article  CAS  Google Scholar 

  40. Comba P, Lang C, de Laorden CL, Muruganantham A, Rajaraman G, Wadepohl H, Zajaczkowski M (2008) Chem Eur J 14:5313–5328

    Article  CAS  Google Scholar 

  41. Bukowski MR, Comba P, Lienke A, Limberg C, de Laorden CL, Mas-Ballesté R, Merz M, Que L Jr (2006) Angew Chem Int Ed 45:3446–3449

    Article  CAS  Google Scholar 

  42. Someya CI, Inoue S, Krackl S, Irran E, Enthaler S (2012) Eur J Inorg Chem 1269–1277

  43. Sammhammer A, Holzgrabe U, Haller R (1989) Arch Pharm 322:551–555

    Article  Google Scholar 

  44. Holzgrabe U, Erciyas E (1992) Arch Pharm 325:657–663

    Article  CAS  Google Scholar 

  45. Comba P, Nuber B, Ramlow A (1997) J Chem Soc Dalton Trans 3:347–352

    Article  Google Scholar 

  46. Alacid E, Nájera C (2008) Org Lett 10:5011–5014

    Article  CAS  Google Scholar 

  47. Sun G, Wang Z (2008) Tetrahedron Lett 49:4929–4932

    Article  CAS  Google Scholar 

  48. Burns MJ, Fairlamb IJS, Kapdi AR, Sehnal P, Taylor RJK (2007) Org Lett 26:5397–5400

    Article  Google Scholar 

  49. Amatore M, Gosmini C (2008) Chem Commun 5019–5021

  50. Cho C-H, Sun M, Seo Y-S, Kim C-B, Park K (2005) J Org Chem 70:1482–1485

    Article  CAS  Google Scholar 

  51. Wu GG, Chen FX, LaFrance D, Liu Z, Greene SG, Wong Y-S, Xie J (2011) Org Lett 13:5220–5223

    Article  CAS  Google Scholar 

  52. Blachut D, Szawkalo J, Czarnocki Z (2011) Synthesis 21:3496–3506

    Google Scholar 

  53. Smit C, Fraaije MW, Minnaard AJ (2008) J Org Chem 73:9482–9485

    Article  CAS  Google Scholar 

  54. Rubottom GM, Evain EJ (1990) Tetrahedron 46:5055–5064

    Article  CAS  Google Scholar 

  55. Kutney JP, Cable J, Gladstone WAF, Hanssen HW, Nair GV, Torupka EJ, Warnock WDC (1975) Can J Chem 53:1796–1817

    Article  CAS  Google Scholar 

  56. Kato S, Kurata T, Ishiguro S, Fujimaki M (1973) Agric Biol Chem 37:1759–1761

    Article  CAS  Google Scholar 

  57. Sheldrick GM (1997) SHELXL93, Program for the refinement of crystal structures. University of Göttingen, Göttingen

    Google Scholar 

Download references

Acknowledgements

Financial support from the Cluster of Excellence “Unifying Concepts in Catalysis” (funded by the Deutsche Forschungsgemeinschaft and administered by the Technische Universität Berlin) is gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Stephan Enthaler.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Haberberger, M., Someya, C.I., Company, A. et al. Application of a Nickel-Bispidine Complex as Pre-Catalyst for C(sp 2)–C(sp 3) Bond Formations. Catal Lett 142, 557–565 (2012). https://doi.org/10.1007/s10562-012-0806-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-012-0806-4

Keywords

Navigation