Skip to main content
SpringerLink
Log in

Nickel-Catalyzed [2+2+2] Cycloaddition of 1,2-o-Carboryne with Alkynes

  • Chapter
  • First Online:
Late Transition Metal-Carboryne Complexes

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

  • 514 Accesses

Abstract

Reactivity studies showed that 1,2-o-carboryne can react with alkenes, dienes, and alkynes in 0[2+2], [2+4] cycloaddition and ene-reaction patterns, similar to that of benzyne. The carboryne reactions are usually complicated and not in a controlled manner. On the other hand, nickel-1,2-o-carboryne complex (η 2-C2B10H10)Ni(PPh3)2 can undergo regioselective [2+2+2] cycloaddition reactions with 2 equiv of alkynes to afford benzocarboranes.

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. Gingrich HL, Ghosh T, Huang Q, Jones M Jr (1990) J Am Chem Soc 112:4082

    Article  CAS  Google Scholar 

  2. Ghosh T, Gingrich HL, Kam CK, Mobraaten ECM, Jones M Jr (1991) J Am Chem Soc 113:1313

    Article  CAS  Google Scholar 

  3. Huang Q, Gingrich HL, Jones M Jr (1991) Inorg Chem 30:3254

    Article  CAS  Google Scholar 

  4. Cunningham RT, Bian N, Jones M Jr (1994) Inorg Chem 33:4811

    Article  CAS  Google Scholar 

  5. Ho DM, Cunningham RJ, Brewer JA, Bian N, Jones M Jr (1995) Inorg Chem 34:5274

    Article  CAS  Google Scholar 

  6. Barnett-Thamattoor L, Zheng G, Ho DM, Jones M Jr, Jackson JE (1996) Inorg Chem 35:7311

    Article  CAS  Google Scholar 

  7. Atkins JH, Ho DM, Jones M Jr (1996) Tetrahedron Lett 37:7217

    Article  CAS  Google Scholar 

  8. Lee T, Jeon J, Song KH, Jung I, Baik C, Park K-M, Lee SS, Kang SO, Ko J (2004) Dalton Trans 933

    Google Scholar 

  9. Jeon J, Kitamura T, Yoo B-W, Kang SO, Ko J (2001) Chem Commun 2110

    Google Scholar 

  10. Sayler AA, Beall H, Sieckhaus JF (1973) J Am Chem Soc 95:5790

    Article  CAS  Google Scholar 

  11. Deng L, Chan H-S, Xie Z (2006) J Am Chem Soc 128:7728

    Article  CAS  Google Scholar 

  12. Schore NE (1988) Chem Rev 88:1081

    Article  CAS  Google Scholar 

  13. Trost BM (1991) Science 254:1471

    Article  CAS  Google Scholar 

  14. Lautens M, Klute W, Tam W (1996) Chem Rev 96:49

    Article  CAS  Google Scholar 

  15. Saito S, Yamamoto Y (2000) Chem Rev 100:2901

    Article  CAS  Google Scholar 

  16. Buchwald SL, Nielsen RB (1988) Chem Rev 88:1047

    Article  CAS  Google Scholar 

  17. Bennett MA, Schwemlein HP (1989) Angew Chem Int Ed Engl 28:1296

    Article  Google Scholar 

  18. Bennett MA, Wenger E (1997) Chem Ber 130:1029

    Article  CAS  Google Scholar 

  19. Jones WM, Klosin J (1998) Adv Organomet Chem 42:147

    Article  CAS  Google Scholar 

  20. Retbøll M, Edwards AJ, Rae AD, Willis AC, Bennett MA, Wenger E (2002) J Am Chem Soc 124:8348

    Article  Google Scholar 

  21. Peña D, Escudero S, Pérez D, Guitián E, Castedo L (1998) Angew Chem Int Ed 37:2659

    Article  Google Scholar 

  22. Peña D, Pérez D, Guitián E, Castedo L (1999) Org Lett 1:1555

    Article  Google Scholar 

  23. Romero C, Peña D, Pérez D, Guitián E (2006) Chem Eur J 12:5677

    Article  CAS  Google Scholar 

  24. Peña D, Pérez D, Guitián E, Castedo L (1999) J Am Chem Soc 121:5827

    Article  Google Scholar 

  25. Radhakrishnan KV, Yoshikawa E, Yamamoto Y (1999) Tetrahedron Lett 40:7533

    Article  CAS  Google Scholar 

  26. Peña D, Pérez D, Guitián E, Castedo L (2000) J Org Chem 65:6944

    Article  Google Scholar 

  27. Sato Y, Tamura T, Mori M (2004) Angew Chem Int Ed 43:2436

    Article  CAS  Google Scholar 

  28. Romero C, Peña D, Pérez D, Guitián E (2008) J Org Chem 73:7996

    Article  CAS  Google Scholar 

  29. Yoshikawa E, Radhakrishnan KV, Yamamoto Y (2000) J Am Chem Soc 122:7280

    Article  CAS  Google Scholar 

  30. Yoshikawa E, Yamamoto Y (2000) Angew Chem Int Ed 39:173

    Article  CAS  Google Scholar 

  31. Quintana I, Boersma AJ, Peña D, Pérez D, Guitián E (2006) Org Lett 8:3347

    Article  CAS  Google Scholar 

  32. Jeganmohan M, Cheng C-H (2004) Org Lett 6:2821

    Article  CAS  Google Scholar 

  33. Jayanth TT, Jeganmohan M, Cheng C-H (2005) Org Lett 7:2921

    Article  CAS  Google Scholar 

  34. Henderson JL, Edwards AS, Greaney MF (2006) J Am Chem Soc 128:7426

    Article  CAS  Google Scholar 

  35. Bhuvaneswari S, Jeganmohan M, Yang M-C,Cheng C-H (2008) Chem Commun 2158

    Google Scholar 

  36. Xie C, Liu L, Zhang Y, Xu P (2008) Org Lett 10:2393

    Article  CAS  Google Scholar 

  37. Bhuvaneswari S, Jeganmohan M, Cheng C-H (2008) Chem Commun 5013

    Google Scholar 

  38. Jeganmohan M, Bhuvaneswari S, Cheng C-H (2009) Angew Chem Int Ed 48:391

    Article  CAS  Google Scholar 

  39. Henderson JL, Edwards AS, Greaney MF (2007) Org Lett 9:5589

    Article  CAS  Google Scholar 

  40. Liu Z, Zhang X, Larock RC (2005) J Am Chem Soc 127:15716

    Article  CAS  Google Scholar 

  41. Liu Z, Larock RC (2007) Angew Chem Int Ed 46:2535

    Article  CAS  Google Scholar 

  42. Bhuvaneswari S, Jeganmohan M, Cheng C-H (2006) Org Lett 8:5581

    Article  CAS  Google Scholar 

  43. Hsieh J-C, Cheng C-H (2005) Chem Commun 2459

    Google Scholar 

  44. Jayanth TT, Cheng C-H (2007) Angew Chem Int Ed 46:5921

    Article  CAS  Google Scholar 

  45. Bennett MA, Glewis M, Hockless DCR, Wenger E (1997) J Chem Soc Dalton Trans 3105

    Google Scholar 

  46. Bennett MA, Macgregor SA, Wenger E (2001) Helv Chim Acta 84:3084

    Article  CAS  Google Scholar 

  47. Deng L, Chan H-S, Xie Z (2006) J Am Chem Soc 128:7728

    Article  CAS  Google Scholar 

  48. Jhingan AK, Maier WF (1987) J Org Chem 52:1161

    Article  CAS  Google Scholar 

  49. Miyaura M (2002) Cross-coupling reactions. A practical guide in topics in current chemistry. Springer, Berlin

    Google Scholar 

  50. Terao J, Tomita M, Singh SP, Kambe N (2010) Angew Chem Int Ed 49:144

    CAS  Google Scholar 

  51. Xie Z (2006) Coord Chem Rev 250:259

    Article  CAS  Google Scholar 

  52. Sun Y, Chan H-S, Zhao H, Lin Z, Xie Z (2006) Angew Chem Int Ed 45:5533

    Article  CAS  Google Scholar 

  53. Sun Y, Chan H-S, Xie Z (2006) Organometallics 25:3447

    Article  CAS  Google Scholar 

  54. Shen H, Xie Z (2009) Chem Commun 2431

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, The Chinese University of Hong Kong, Shatin, N. T.,, Hong Kong, People’s Republic of China

    Zaozao Qiu

Authors
  1. Zaozao Qiu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zaozao Qiu .

Rights and permissions

Reprints and permissions

Copyright information

© 2012 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Qiu, Z. (2012). Nickel-Catalyzed [2+2+2] Cycloaddition of 1,2-o-Carboryne with Alkynes. In: Late Transition Metal-Carboryne Complexes. Springer Theses. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-24361-5_5

Download citation

Publish with us

Policies and ethics

Search

Navigation