Skip to main content
Log in

Recent Advances in the Pauson–Khand Reaction

  • Original Paper
  • Published:
Topics in Catalysis Aims and scope Submit manuscript

Abstract

The Pauson–Khand [2+2+1] cycloaddition of alkynes, alkenes, and carbon monoxide has been a vibrant area of research for more than 40 years. This review highlights recent achievements in the Pauson–Khand reaction, particularly in catalytic and asymmetric variants. Discussion of regioselectivity and advances in substrate scope is also presented.

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
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Scheme 11
Scheme 12
Fig. 1
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17
Scheme 18
Scheme 19
Scheme 20
Scheme 21
Scheme 22

Similar content being viewed by others

References

  1. Pauson PL, Khand IU, Knox GR, Watts WE (1971) J Chem Soc D 1:36

    Google Scholar 

  2. Khand U, Knox GR, Pauson PL, Watts WE (1973) J Chem Soc Perkin Trans 1:975–977

    Article  Google Scholar 

  3. Khand U, Knox GR, Pauson PL, Watts WE, Foreman MI (1973) J Chem Soc Perkin Trans 1:977–981.

    Article  Google Scholar 

  4. Torres RR (2012) The Pauson–Khand reaction. Scope, variations and applications. Wiley, New York

    Book  Google Scholar 

  5. Turlington M, Du Y, Ostrum SG, Santosh V, Wren K, Lin T, Sabat M, Pu L (2011) J Am Chem Soc 133:11780–11794

    Article  CAS  Google Scholar 

  6. Huang J, Fang L, Long R, Shi L-L, Shen H-J, Li C-C, Yang Z (2013) Org Lett 15:4018–4021

    Article  CAS  Google Scholar 

  7. McKerrall SJ, Jorgensen L, Kuttruff CA, Ungeheuer F, Baran PS (2014) J Am Chem Soc 136:5799–5810

    Article  CAS  Google Scholar 

  8. Williams DR, Shah AA (2014) J Am Chem Soc 136:8829–8836

    Article  CAS  Google Scholar 

  9. You L, Liang X-T, Xu L-M, Wang Y-F, Zhang J-J, Su Q, Li Y-H, Zhang B, Yang S-L, Chen J-H, Yang Z (2015) J Am Chem Soc 137:10120–10123

    Article  CAS  Google Scholar 

  10. Clark JS, Xu C (2016) Angew Chem Int Ed 55:4332–4335

    Article  CAS  Google Scholar 

  11. Chuang KV, Xu C, Reisman SE (2016) Science 353:912–915

    Article  CAS  Google Scholar 

  12. Baik M-H, Mazumder S, Ricci P, Sawyer JR, Song Y-G, Wang H, Evans PA (2011) J Am Chem Soc 133:7621–7623

    Article  CAS  Google Scholar 

  13. Kent JL, Wan H, Brummond KM (1995) Tetrahedron Lett 36:2407–2410

    Article  CAS  Google Scholar 

  14. Ahmar M, Antras F, Cazes B (1995) Tetrahedron Lett 36:4417–4420

    Article  CAS  Google Scholar 

  15. Schore NE (1991) Org React 40:1–90

    CAS  Google Scholar 

  16. Antras F, Laurent S, Ahmar M, Chermette H, Cazes B (2010) Eur J Org Chem 17:3312–3336

    Article  Google Scholar 

  17. Greenfield H, Wender I, Wotiz JH (1956) J Org Chem 21:875–878

    Article  CAS  Google Scholar 

  18. Sóvágó J, Newton MG, Mushina EA, Ungváry F (1996) J Am Chem Soc 118:9589–9596

    Article  Google Scholar 

  19. Magnus P, Principe LM (1985) Tetrahedron Lett 26:4851–4854

    Article  CAS  Google Scholar 

  20. Williams DR, Shah AA, Mazumder S, Baik M-H (2013) Chem Sci 4:238–247

    Article  CAS  Google Scholar 

  21. Lledó A, Fuster A, Revés M, Verdaguer A, Riera A (2013) Chem Commun 49:3055–3057

    Article  Google Scholar 

  22. Khand U, Pauson PL (1976) J Chem Soc Perkin Trans 1:30–32

    Article  Google Scholar 

  23. MacWhorter SE, Sampath V, Olmstead MM, Shore NE (1988) J Org Chem 53:203–205

    Article  CAS  Google Scholar 

  24. Mayo P, Tam W (2001) Tetrahedron 57:5943–5952

    Article  CAS  Google Scholar 

  25. Aiguabella N, Pesquer A, Verdaguer X, Riera A (2013) Org Lett 15:2696–2699

    Article  CAS  Google Scholar 

  26. Turlington M, Yue Y, Yu X-Q, Pu L (2010) J Org Chem 75:6941–6952

    Article  CAS  Google Scholar 

  27. Garcia Ruano JL, Torrente E, Parra A, Aleman J, Martin-Castro AM (2012) J Org Chem 77:6583–6599

    Article  CAS  Google Scholar 

  28. Fustero S, Lazaro R, Aiguabella N, Riera A, Simon-Fuentes, Barrio P (2014) Org Lett 16:1224–1227

    Article  CAS  Google Scholar 

  29. Hong B-C, Dange NS, Yen P-J, Lee G-H, Liao J-H (2012) Org Lett 14:5346–5349

    Article  CAS  Google Scholar 

  30. Shi L-L, Shen H-J, Fang L-C, Huang J, Li C-C, Yang Z (2013) Chem Commun 49:8806–8808

    Article  CAS  Google Scholar 

  31. Yadav J, Stanton GR, Fan X, Robinson JR, Schelter EJ, Walsh PJ, Pericas MA (2014) Chem Eur J 20:7122–7127

    Article  CAS  Google Scholar 

  32. Grillet F, Huang C, Brummond KM (2011) Org Lett 13:6304–6307

    Article  CAS  Google Scholar 

  33. Chen W, Tay J-H, Ying J, Yu X-Q, Pu L (2013) J Org Chem 78:2256–2265

    Article  CAS  Google Scholar 

  34. Furusawa T, Morimoto T, Ikeda K, Tanimoto H, Nishiyama H, Kakiuchi K, Jeong N (2015) Tetrahedron 71:875–881

    Article  CAS  Google Scholar 

  35. Krafft ME, Scott IL, Romero RH, Feibelmann S, Van Pelt CE (1993) J Am Chem Soc 115:7199–7207

    Article  CAS  Google Scholar 

  36. Orgue S, Leon T, Riera A, Verdaguer X (2015) Org Lett 17:250–253

    Article  CAS  Google Scholar 

  37. Cristobal-Lecina E, Costantino AR, Grabulosa A, Riera A, Verdaguer X (2015) Organometallics 34:4989–4993

    Article  CAS  Google Scholar 

  38. Cristobal-Lecina E, Etavo P, Doran S, Reves M, Martin-Gago P, Grabulosa AR, Vidal-Ferran A, Riera A, Verdaguer X (2014) Adv Synth Catal 356:795–804

    Article  CAS  Google Scholar 

  39. Mottalib MA, Haukka M, Nordlander E (2016) Polyhedron Part B 103:275–282.

    Article  CAS  Google Scholar 

  40. Krafft ME, Bonaga LVR, Hirosawa C (2001) J Org Chem 66:3004–3020

    Article  CAS  Google Scholar 

  41. Lee HY, An M, Sohn J-H (2003) Bull Korean Chem Soc 24:539–540.

    Article  CAS  Google Scholar 

  42. Moulton BE, Whitwood AC, Duhme-Klair AK, Lynam JM, Fairlamb IJS (2011) J Org Chem 76:5320–5334

    Article  CAS  Google Scholar 

  43. Fager-Jokela E, Muuronen M, Patzschke M, Helaja J (2012) J Org Chem 77:9134–9147

    Article  CAS  Google Scholar 

  44. Fager-Jokela E, Muuronen M, Khaizourane H, Vázquez-Romero A, Verdaguer X, Riera A, Helaja J (2014) J Org Chem 79:10999–11010

    Article  CAS  Google Scholar 

  45. Aiguabella N, del Pozo C, Verdaguer X, Fustero S, Riera A (2013) Angew Chem Int Ed 52:5355–5399

    Article  CAS  Google Scholar 

  46. León T, Fernández E (2016) Chem Commun 52:9363–9366

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Laina M. Geary.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ricker, J.D., Geary, L.M. Recent Advances in the Pauson–Khand Reaction. Top Catal 60, 609–619 (2017). https://doi.org/10.1007/s11244-017-0741-0

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11244-017-0741-0

Keywords

Navigation