Skip to main content
SpringerLink
Log in

Palladium Catalyzed Cascade Reactions Involving π-Allyl Palladium Chemistry

  • Chapter
  • First Online:
Metal Catalyzed Cascade Reactions

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 19))

Abstract

Palladium-catalyzed cascade reactions have gained steadily increasing importance over the last decade. The important factor in these reactions is the catalytic generation of π-allyl palladium intermediates which further undergo a variety of reactions. π-Allyl palladium complexes can be easily formed by the treatment of allylic substrates with Pd(0). A π-allyl palladium complexes on treatment with allylic metal species produce bis π-allyl palladium complex. In this review, the palladium catalyzed cascade reactions involving π-allyl palladium chemistry is described. The first part deals with catalytic reactions involving π-allyl palladium complexes as an intermediate, while the second part features catalytic reactions involving bis π-allyl palladium complex as an intermediate.

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

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

Ac:

acetyl

Ar:

aryl

dba:

dibenzylideneacetone

dppf:

1,1′-bis(diphenylphosphino)ferrocene

dppp:

1,3-bis(diphenylphosphino)propane

dppe:

1,2-bis(diphenylphosphino)ethane

ee:

enantiomer excess

TBAB:

tetrabutylammonium bromide

THF:

tetrahydrofuran

TMS:

trimethylsilyl

Ts:

tosyl

rt:

room temperature

References

  1. Poli G, Giambastiani G, Heumann A (2000) Tetrahedron 56:5959

    Article  CAS  Google Scholar 

  2. Heumann A, Reglier M (1996) Tetrahedron 52:9289

    Article  CAS  Google Scholar 

  3. Meijere AD, Brase S (1999) J Organomet Chem 576:88

    Article  Google Scholar 

  4. Tietze LF (1996) Chem Rev 96:115

    Article  CAS  Google Scholar 

  5. Balme G, Bossharth E, Monteiro N (2003) Eur J Org Chem 4101

    Google Scholar 

  6. Ramon DJ, Yus M (2005) Angew Chem Int Ed 44:1602

    Article  CAS  Google Scholar 

  7. Tejedor D, Gonzalez-Cruz D, Santos-Exposito A, Marrero-Tellado JJ, Armas PD, Garcia-Tellado F (2005) Chem Eur J 11:3502

    Article  CAS  Google Scholar 

  8. Meijere AD, Zezschwitz PV, Brase S (2005) Acc Chem Res 38:413

    Article  Google Scholar 

  9. Tsuji J (2000) Transition Metal Reagents and Catalysts, chap 4. Wiley, New York

    Google Scholar 

  10. Trost BM, Van Vranken DL (1996) Chem Rev 96:395

    Article  CAS  Google Scholar 

  11. Johannsen M, Jorgensen KA (1998) Chem Rev 98:1689

    Article  CAS  Google Scholar 

  12. Gevorgyan V, Kadowaki C, Salter MM, Kadota I, Saito S, Yamamoto Y (1997) Tetrahedron Lett 53:9097

    CAS  Google Scholar 

  13. Radhakrishnan U, Al-Masum M, Yamamoto Y (1998) Tetrahedron Lett 39:1037

    Article  CAS  Google Scholar 

  14. Minami I, Yuhara M, Watanabe H, Tsuji J (1987) J Organomet Chem 334:225

    Article  CAS  Google Scholar 

  15. Tsuji J, Mandai T (1995) Angew Chem Int Ed Engl 34:2589

    Article  CAS  Google Scholar 

  16. Kozawa Y, Mori M (2002) Tetrahedron Lett 43:1499

    Article  CAS  Google Scholar 

  17. Yoshida M, Nemoto H, Ihara M (1999) Tetrahedron Lett 40:8583

    Article  CAS  Google Scholar 

  18. Fournier-Nguefack C, Lhoste P, Sinou D (1996) Synlett 553

    Google Scholar 

  19. Kozawa Y, Mori M (2003) J Org Chem 68:8068

    Article  CAS  Google Scholar 

  20. Labrosse J-R, Lhoste P, Sinou D (1999) Tetrahedron Lett 40:9025

    Article  CAS  Google Scholar 

  21. Damez C, Labrosse J-R, Lhoste P, Sinou D (2003) Tetrahedron Lett 44:557

    Article  CAS  Google Scholar 

  22. Labrosse J-R, Lhoste P, Sinou D (2000) Org Lett 2:527

    Article  CAS  Google Scholar 

  23. Szabo KJ (2004) Chem Eur J 10:5268

    Article  CAS  Google Scholar 

  24. Trost BM, Crawley ML (2003) Chem Rev 103:2921

    Article  CAS  Google Scholar 

  25. Trost BM (2004) J Org Chem 69:5813

    Article  CAS  Google Scholar 

  26. Heumann A, Reglier M (1995) Tetrahedron 51:975

    Article  CAS  Google Scholar 

  27. Nakamura H, Iwama H, Yamamoto Y (1996) J Am Chem Soc 118:6641

    Article  CAS  Google Scholar 

  28. Bao M, Nakamura H, Yamamoto Y (2000) Tetrahedron Lett 41:131

    Article  CAS  Google Scholar 

  29. Nakamura H, Nakamura K, Yamamoto Y (1998) J Am Chem Soc 120:4242

    Article  CAS  Google Scholar 

  30. Nakamura K, Nakamura H, Yamamoto Y (1999) J Org Chem 64:2614

    Article  CAS  Google Scholar 

  31. Fernandes RA, Yamamoto Y (2003) J Org Chem 69:735

    Article  Google Scholar 

  32. Fernandes RA, Stimac A, Yamamoto Y (2003) J Am Chem Soc 125:14133

    Article  CAS  Google Scholar 

  33. Nakamura H, Shim J-G, Yamamoto Y (1997) J Am Chem Soc 119:8113

    Article  CAS  Google Scholar 

  34. Henc B, Jolly PW, Salz R, Wilke G, Benn R, Hoffman EG, Mynott R, Schroth G, Seevolgel K, Sekutowski JC, Kruger C (1980) J Organomet Chem 191:425

    Article  CAS  Google Scholar 

  35. Goliaszewski A, Schwartz J (1984) J Am Chem Soc 106:5028

    Article  CAS  Google Scholar 

  36. Goliaszewski A, Schwartz J (1985) Tetrahedron 41:5779

    Article  CAS  Google Scholar 

  37. Nakamura H, Sekido M, Ito M, Yamamoto Y (1998) J Am Chem Soc 120:6838

    Article  CAS  Google Scholar 

  38. Xie RL, Hauske JR (2000) Tetrahedron Lett 41:10167

    Article  CAS  Google Scholar 

  39. Aoyagi K, Nakamura H, Yamamoto Y (2002) J Org Chem 67:5977

    Article  CAS  Google Scholar 

  40. Nakamura H, Shibata H, Yamamoto Y (2000) Tetrahedron Lett 41:2911

    Article  CAS  Google Scholar 

  41. Sekido M, Aoyagi K, Nakamura H, Kabuto C, Yamamoto Y (2001) J Org Chem 66:7142

    Article  CAS  Google Scholar 

  42. Shim J-G, Yamamoto Y (1998) J Org Chem 63:3067

    Article  CAS  Google Scholar 

  43. Shim J-G, Yamamoto Y (1999) Tetrahedron Lett 40:1053

    Article  CAS  Google Scholar 

  44. El AB, Alper H (1999) In: Murahashi S-I, Davies SG (eds) Transition Metal Catalysed Reaction. Blackwell, Oxford, p 261

    Google Scholar 

  45. Courillon C, Thorimbert S, Malacria M (2000) In: Negishi E (ed) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1795

    Google Scholar 

  46. Larksarp C, Sellier O, Alper H (2001) J Org Chem 66:3502

    Article  CAS  Google Scholar 

  47. Meguro M, Yamamoto Y (1999) J Org Chem 64:694

    Article  CAS  Google Scholar 

  48. Nakamura I, Oh BH, Saito S, Yamamoto Y (2001) Angew Chem Int Ed 40:1298

    Article  CAS  Google Scholar 

  49. Oh BH, Nakamura I, Saito S, Yamamoto Y (2001) Tetrahedron Lett 42:6203

    Article  CAS  Google Scholar 

  50. Siriwardana AI, Nakamura I, Yamamoto Y (2004) J Org Chem 69:3202

    Article  CAS  Google Scholar 

  51. Kamijo S, Jin T, Huo Z, Yamamoto Y (2002) Tetrahedron Lett 43:9707

    Article  CAS  Google Scholar 

  52. Kamijo S, Jin T, Huo Z, Yamamoto Y (2003) J Am Chem Soc 125:7786

    Article  CAS  Google Scholar 

  53. Kamijo S, Jin T, Huo Z, Yamamoto Y (2004) J Org Chem 69:2386

    Article  CAS  Google Scholar 

  54. Kamijo S, Jin T, Yamamoto Y (2004) Tetrahedron Lett 45:689

    Article  CAS  Google Scholar 

  55. Kamijo S, Jin T, Yamamoto Y (2002) J Org Chem 67:7413

    Article  CAS  Google Scholar 

  56. Gyoung YS, Shim JG, Yamamoto Y (2000) Tetrahedron Lett 41:4193

    Article  CAS  Google Scholar 

  57. Cacchi S, Fabrizi G, Pace P (1998) J Org Chem 63:1001

    Article  CAS  Google Scholar 

  58. Cacchi S, Fabrizi G, Moro L (1998) Synlett 7:741

    Google Scholar 

  59. Monteiro N, Balme G (1998) Synlett 746

    Google Scholar 

  60. Kamijo S, Yamamoto Y (2002) J Am Chem Soc 124:11940

    Article  CAS  Google Scholar 

  61. Kamijo S, Jin T, Yamamoto Y (2001) J Am Chem Soc 123:9453

    Article  CAS  Google Scholar 

  62. Xie X, Lu X (1999) Tetrahedron Lett 40:8415

    Article  CAS  Google Scholar 

  63. Ma S, Jiao N (2002) Angew Chem Int Ed 41:4737

    Article  CAS  Google Scholar 

  64. Nakamura I, Saito S, Yamamoto Y (2000) J Am Chem Soc 122:2661

    Article  CAS  Google Scholar 

  65. Nakamura I, Siriwardana AI, Saito S, Yamamoto Y (2002) J Org Chem 67:3445

    Article  CAS  Google Scholar 

  66. Yoshida M, Ihara M (2001) Angew Chem Int Ed 40:616

    Article  CAS  Google Scholar 

  67. Yoshida M, Fujita M, Ihara M (2003) Org Lett 3:3325

    Article  Google Scholar 

  68. Yoshida M, Fujita M, Ishii T, Ihara M (2003) J Am Chem Soc 125:4874

    Article  CAS  Google Scholar 

  69. Yoshida M, Komatsuzaki Y, Nemoto H, Ihara M (2004) J Chem Soc Perkin 1 2:3099

    CAS  Google Scholar 

  70. Yoshida M, Nemoto H, Ihara M (2004) Tetrahedron Lett 40:8583

    Article  Google Scholar 

  71. Yoshida M, Sugimoto K, Ihara M (2002) Tetrahedron 58:7839

    Article  CAS  Google Scholar 

  72. Tietze LF, Nordmann G (2001) E J Org Chem 3247

    Google Scholar 

  73. Nakamura H, Aoyagi K, Shim JG, Yamamoto Y (2001) J Am Chem Soc 123:372

    Article  CAS  Google Scholar 

  74. Solin N, Narayan S, Szabo KJ (2001) Org Lett 3:909

    Article  CAS  Google Scholar 

  75. Wallner OA, Szabo KJ (2003) J Org Chem 68:2934

    Article  CAS  Google Scholar 

  76. Shim J-G, Nakamura H, Yamamoto Y (1998) J Org Chem 63:8470

    Article  CAS  Google Scholar 

  77. Yoshikawa E, Radhakrishnan KV, Yamamoto Y (2000) Tetrahedron Lett 41:729

    Article  CAS  Google Scholar 

  78. Nakamura H, Ohtaka M, Yamamoto Y (2002) Tetrahedron Lett 43:7631

    Article  CAS  Google Scholar 

  79. Ohtaka M, Nakamura H, Yamamoto Y (2004) Tetrahedron Lett 45:7339

    Article  CAS  Google Scholar 

  80. Kamijo S, Yamamoto Y (2002) Angew Chem Int Ed 41:3230

    Article  CAS  Google Scholar 

  81. Bao M, Nakamura H, Inoue A, Yamamoto Y (2002) Chem Lett 158

    Google Scholar 

  82. Bao M, Nakamura H, Yamamoto Y (2001) J Am Chem Soc 123:759

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Graduate School of Science, Tohoku University, 980-8578, Sendai, Japan

    Nitin T. Patil & Yoshinori Yamamoto

Authors
  1. Nitin T. Patil
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yoshinori Yamamoto
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yoshinori Yamamoto .

Editor information

Thomas J. J. Müller

Rights and permissions

Reprints and permissions

About this chapter

Cite this chapter

Patil, N.T., Yamamoto, Y. Palladium Catalyzed Cascade Reactions Involving π-Allyl Palladium Chemistry. In: Müller, T.J.J. (eds) Metal Catalyzed Cascade Reactions. Topics in Organometallic Chemistry, vol 19. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_014

Download citation

Publish with us

Policies and ethics

Search

Navigation