Skip to main content

Palladium(IV) Complexes as Intermediates in Catalytic and Stoichiometric Cascade Sequences Providing Complex Carbocycles and Heterocycles

  • Chapter
  • First Online:
Higher Oxidation State Organopalladium and Platinum Chemistry

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 35))

Abstract

Palladium-catalyzed multicomponent coupling and annulation reactions have become important tools in organic synthesis. Recently, palladium(IV) complexes have been proposed as intermediates in catalytic cycles of these transformations, although experimental evidence for their involvement is frequently lacking. Examples of such catalytic annulation reactions are discussed, followed by a review of studies performed with stoichiometric isolable or semistable palladium(IV) complexes seeking experimental evidence for feasibility of the participation of palladium(IV) intermediates in cascade carbon–carbon and carbon–heteroatom bond-forming sequences.

Graphical Abstract

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

Access this chapter

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. Negishi EI, Coperet C, Ma S, Liou SY, Li F (1996) Chem Rev 96:365

    Article  CAS  Google Scholar 

  2. Dyker G (1992) Angew Chem Int Ed Engl 31:1023

    Article  Google Scholar 

  3. Dyker G (1993) J Org Chem 58:6426

    Article  CAS  Google Scholar 

  4. Catellani M (2003) Synlett 298

    Google Scholar 

  5. Lautens M, Pache S (2003) Org Lett 5:4827

    Article  Google Scholar 

  6. Gerike KM, Chai DI, Bieler N, Lautens M (2009) Angew Chem Int Ed 48:1447

    Article  Google Scholar 

  7. Sehnal P, Taylor RJK, Farilamb IJS (2010) Chem Rev 110:824

    Article  CAS  Google Scholar 

  8. Faccini F, Motti E, Catellani M (2004) J Am Chem Soc 126:78

    Article  CAS  Google Scholar 

  9. Dell Ca N, Motti E, Mega A, Catellani M (2010) Adv Synth Catal 352:1451

    Google Scholar 

  10. Cardenas DJ, Marin-Matute B, Echavarren AM (2006) J Am Chem Soc 128:5033

    Article  CAS  Google Scholar 

  11. Larock RC, Campo MA (2002) J Am Chem Soc 124:14326

    Article  Google Scholar 

  12. Mota AJ, Dedieu A (2006) Organometallics 25:3130

    Article  CAS  Google Scholar 

  13. Tang S, Peng P, Pi SF, Liang Y, Wang NW, Li JH (2008) Org Lett 10:1179

    Article  CAS  Google Scholar 

  14. Muniz K, Hovelmann CH, Streuff J (2008) J Am Chem Soc 130:763

    Article  CAS  Google Scholar 

  15. Liu G, Stahl SS (2006) J Am Chem Soc 128:7179

    Article  CAS  Google Scholar 

  16. Rosewall CF, Sibbald PA, Liskin DV, Michael FE (2009) J Am Chem Soc 131:9488

    Article  CAS  Google Scholar 

  17. Canty AJ, Hoare JL, Davies NL, Traill PR (1998) Organometallics 17:2046

    Article  CAS  Google Scholar 

  18. Byers PK, Canty AJ, Traill PR, Watson AA (1990) J Organomet Chem 390:399

    Article  CAS  Google Scholar 

  19. Brown DG, Byers PK, Canty AJ (1990) Organometallics 9:1231

    Article  CAS  Google Scholar 

  20. van Belzen R, Klein RA, Kooijman H, Veldman N, Spek AL, Elsevier CJ (1998) Organometallics 17:1812

    Article  Google Scholar 

  21. van Belzen R, Elsevier CJ (2003) Organometllics 22:722

    Article  Google Scholar 

  22. Bocelli G, Catellani M, Ghelli S (1993) J Organomet Chem 458:C12

    Article  CAS  Google Scholar 

  23. Amatore C, Catallani M, Deledda S, Jutand A, Motti E (2008) Organometallics 27:4549

    Article  CAS  Google Scholar 

  24. Yamamoto Y, Kuwabara S, Matsuo S, Ohno T, Nishiyama H, Itoh K (2004) Organometallics 23:3898

    Article  CAS  Google Scholar 

  25. Guo R, Portscheller JL, Day VW, Malinakova HC (2007) Organometallics 26:3874

    Article  CAS  Google Scholar 

  26. Datta Chaudhuri P, Guo R, Malinakova HC (2008) J Organomet Chem 693:567

    Google Scholar 

  27. Lu G, Portscheller JL, Malinakova HC (2005) Organometallics 24:945

    Article  CAS  Google Scholar 

  28. Canty AJ (1992) Acc Chem Res 25:83

    Article  CAS  Google Scholar 

  29. Powers DC, Ritter T (2009) Nat Chem 1:302

    Google Scholar 

  30. Racowski JM, Dick AR, Sanford MS (2009) J Am Chem Soc 131:10974

    Article  CAS  Google Scholar 

  31. Canty AJ, Patel J, Rodemann T, Ryan JH, Skelton BW, White AH (2004) Organometallics 23:3466

    Article  CAS  Google Scholar 

  32. Caty AJ, Gardiner MG, Jones RC, Rodemann T, Sharma M (2009) J Am Chem Soc 131:7236

    Article  Google Scholar 

  33. Pilarski, LT, Selander N, Böse D, Szabó KJ (2009) Org Lett 11:5518

    Google Scholar 

  34. Aydin J, Larsson JM, Selander N, SzabĂł KJ (2009) Org Lett 11:2852

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Helena C. Malinakova .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2011 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Malinakova, H.C. (2011). Palladium(IV) Complexes as Intermediates in Catalytic and Stoichiometric Cascade Sequences Providing Complex Carbocycles and Heterocycles. In: Canty, A. (eds) Higher Oxidation State Organopalladium and Platinum Chemistry. Topics in Organometallic Chemistry, vol 35. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-17429-2_4

Download citation

Publish with us

Policies and ethics