Skip to main content

Catalysis and Organometallic Chemistry of Rhodium and Iridium in the Oxidation of Organic Substrates

  • Chapter
  • First Online:
Organometallic Oxidation Catalysis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 22))

Abstract

The purpose of this chapter is to present a survey of the organometallic chemistry and catalysis of rhodium and iridium related to the oxidation of organic substrates that has been developed over the last 5 years, placing special emphasis on reactions or processes involving environmentally friendly oxidants. Iridium-based catalysts appear to be promising candidates for the oxidation of alcohols to aldehydes/ketones as products or as intermediates for heterocyclic compounds or domino reactions. Rhodium complexes seem to be more appropriate for the oxygenation of alkenes. In addition to catalytic allylic and benzylic oxidation of alkenes, recent advances in vinylic oxygenations have been focused on stoichiometric reactions. This review offers an overview of these reactions as well as some comments on key questions related to achieving the desired C – O bond formation.

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 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
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

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Beller M (2004) Adv Synth Catal 346:107

    Article  CAS  Google Scholar 

  2. Punniyamurthy T, Velusamy S, Iqbal J (2005) Chem Rev 105:2329

    Article  CAS  Google Scholar 

  3. Jones CW (1999) Applications of Hydrogen Peroxide and Derivatives. R Soc Chem, Cambridge

    Google Scholar 

  4. Moiseev II (1997) J Mol Catal A 127:1

    Article  CAS  Google Scholar 

  5. Bäckvall JE (ed) (2004) Modern Oxidation Methods. Wiley, Weinheim

    Google Scholar 

  6. Simándi LI (ed) (2003) Advances in Catalytic Activation of Dioxygen by Metal Complexes. Kluwer, Dordrecht

    Google Scholar 

  7. Hill HAO, Tew DG (1987) Dioxygen, Peroxide and Superoxide. In: Wilkinson G, Gillard RD, McCleverty JA (eds) Comprehensive Coordination Chemistry, vol 2, chap 15.2. Pergamon Press, Oxford, p 315

    Google Scholar 

  8. Peris E, Crabtree RH (2004) Coord Chem Rev 248:2239

    Article  CAS  Google Scholar 

  9. Mimoun H (1987) Metal Complexes in Oxidation. In: Wilkinson G, Gillard RD, McCleverty JA (eds) Comprehensive Coordination Chemistry, vol 6, chap 61.3. Pergamon Press, Oxford, p 317

    Google Scholar 

  10. Drago RS (1992) Coord Chem Rev 117:185

    Article  CAS  Google Scholar 

  11. Read G (1988) J Mol Catal 44:15

    Article  CAS  Google Scholar 

  12. Faraj M, Brégeault JM, Martin J, Martin C (1985) J Organomet Chem 276:C23

    Article  Google Scholar 

  13. Martin C, Faraj M, Martin J, Bregeault JM, Mercier J, Fillaux J, Dizabo P (1986) J Mol Catal 37:201

    Article  CAS  Google Scholar 

  14. Drago RS, Zuzich A, Nyberg ED (1985) J Am Chem Soc 107:2898

    Article  CAS  Google Scholar 

  15. Mimoun H (1981) Pure Appl Chem 53:2389

    CAS  Google Scholar 

  16. Faraj M, Martin J, Martin J, Brégeault JM (1985) J Mol Catal 31:57

    Article  CAS  Google Scholar 

  17. Atlay MT, Preece M, Strukul G, James BR (1982) J Chem Soc Chem Commun 406

    Google Scholar 

  18. Lyons JE, Turner JO (1972) J Org Chem 37:2881

    Article  CAS  Google Scholar 

  19. Morvillo A, Bressan M (1986) J Mol Catal 37:63

    Article  CAS  Google Scholar 

  20. Fusi A, Ugo R, Fox F, Pasini A, Cenini S (1971) J Organomet Chem 26:417

    Article  CAS  Google Scholar 

  21. Lyons JE, Turner JO (1972) Tetrahedron Lett 2903

    Google Scholar 

  22. Müller P, Idmoumaz H (1988) J Organomet Chem 345:187

    Article  Google Scholar 

  23. Read G, Shaw J (1984) J Chem Soc Chem Commun 1313

    Google Scholar 

  24. Mimoun H, Machirant MMP, de Roch IS (1978) J Am Chem Soc 100:5437

    Article  Google Scholar 

  25. James BR, Morriis RH, Kvintovics P (1986) Can J Chem 64:897

    Article  CAS  Google Scholar 

  26. Bressan M, Morandini F, Morvillo A (1985) J Organomet Chem 280:139

    Article  CAS  Google Scholar 

  27. Fowler P, Read G, Shaw J, Šik V (1991) J Chem Soc Dalton Trans 1087

    Google Scholar 

  28. de Bruin B, Budzelaar PHM, Gal AW (2004) Angew Chem Int Ed 43:4142

    Article  CAS  Google Scholar 

  29. Carlton L, Read G, Urgelles M (1983) J Chem Soc Chem Commun 586

    Google Scholar 

  30. Bien S, Segal Y (1977) J Org Chem 42:1685

    Article  CAS  Google Scholar 

  31. Uemura S, Patil SR (1982) Chem Lett 1743

    Google Scholar 

  32. Weiner H, Trovarelli A, Finke RG (2003) J Mol Catal 191:217

    Article  CAS  Google Scholar 

  33. Srinivassan K, Perrier S, Kochi JK (1986) J Mol Catal 36:297

    Article  Google Scholar 

  34. Catino AJ, Forslund RE, Doyle MP (2004) J Am Chem Soc 126:13622

    Article  CAS  Google Scholar 

  35. Catino AJ, Nichols JM, Choi H, Gottipamula S, Doyle MP (2005) Org Lett 7:5167

    Article  CAS  Google Scholar 

  36. Fazlur-Rahman AK, Tsai JJ, Nicholas KM (1992) J Chem Soc Chem Commun 1334

    Google Scholar 

  37. Shi M (1998) J Chem Res (S) 592

    Google Scholar 

  38. Moody CJ, Palmer FN (2002) Tetrahedron Lett 43:139

    Article  CAS  Google Scholar 

  39. Herman WA, Cornils B (1997) Angew Chem Int Ed Engl 36:1049

    Google Scholar 

  40. Crabtree RH, Felkin H, Morris GE (1977) J Organomet Chem 141:205

    Article  CAS  Google Scholar 

  41. Hillier AC, Lee HM, Stevens ED, Nolan SP (2001) Organometallics 20:4246

    Article  CAS  Google Scholar 

  42. Albrecht M, Miecznikowski JR, Samuel A, Faller JW, Crabtree RH (2002) Organometallics 21:3596

    Article  CAS  Google Scholar 

  43. Bäckvall JE (2002) J Organomet Chem 652:105

    Article  Google Scholar 

  44. Pàmies O, Bäckvall JE (2001) Chem Eur J 7:5052

    Article  Google Scholar 

  45. Fujita K, Yamaguchi R (2005) Synlett 560

    Google Scholar 

  46. Fujita K, Furukawa S, Yamaguchi R (2002) J Organomet Chem 649:289

    Article  CAS  Google Scholar 

  47. Suzuki T, Morita K, Tsuchida M, Hiroi K (2003) J Org Chem 68:1601

    Article  CAS  Google Scholar 

  48. Suzuki T, Morita K, Tsuchida M, Hiroi K (2002) Org Lett 4:2361

    Article  CAS  Google Scholar 

  49. Suzuki T, Morita K, Matsuo Y, Hiroi K (2003) Tetrahedron Lett 44:2003

    Article  CAS  Google Scholar 

  50. Hanasaka F, Fujita K, Yamaguchi R (2004) Organometallics 23:1490

    Article  CAS  Google Scholar 

  51. Hanasaka F, Fujita K, Yamaguchi R (2005) Organometallics 24:3422

    Article  CAS  Google Scholar 

  52. Gauthier S, Scopelliti R, Severin K (2004) Organometallics 23:3769

    Article  CAS  Google Scholar 

  53. Ajjou AA (2001) Tetrahedron Lett 42:13

    Article  Google Scholar 

  54. Ajjou AA, Pinet J-L (2005) Can J Chem 83:702

    Article  CAS  Google Scholar 

  55. Morales-Morales D, Redón R, Wang Z, Lee DW, Yung C, Magnuson K, Jensen CM (2001) Can J Chem 79:823

    Article  CAS  Google Scholar 

  56. Jung EM (1976) Tetrahedron 32:3

    Article  CAS  Google Scholar 

  57. Fijita K, Yamamoto K, Yamaguchi R (2002) Org Lett 4:269

    Article  CAS  Google Scholar 

  58. Cho CS, Seok HJ, Shim SC (2005) J Heterocyclic Chem 42:1219

    Article  CAS  Google Scholar 

  59. Cho CS, Kim BT, Kim T-J, Shim SC (2001) Chem Commun 2576

    Google Scholar 

  60. Edwards MG, Williams JMJ (2002) Angew Chem Int Ed 41:4749

    Article  Google Scholar 

  61. Cami-Kobeci G, Williams JMJ (2004) Chem Commun 1072

    Google Scholar 

  62. Taguchi K, Nakagawa H, Hirabayashi T, Sakaguchi S, Ishii Y (2004) J Am Chem Soc 126:72

    CAS  Google Scholar 

  63. Fujita K, Li Z, Ozeki N, Yamaguchi R (2003) Tetrahedron Lett 44:2687

    Article  CAS  Google Scholar 

  64. Deubel DV, Frenking G, Gisdakis P, Herrmann WA, Rösch N, Sundermeyer J (2004) Acc Chem Res 37:645

    Article  CAS  Google Scholar 

  65. Krom M, Coumans RGE, Smits JMM, Gal AW (2001) Angew Chem Int Ed 40:2106

    Article  CAS  Google Scholar 

  66. Krom M, Peters TPJ, Coumans RGE, Sciarone TJJ, Hoogboom J, ter Beek SI, Schlebos PPJ, Smits JMM, de Gelder R, Gal AW (2003) Eur J Inorg Chem 1072

    Google Scholar 

  67. de Bruin B, Verhagen JAW, Schouten CHJ, Gal AW, Feichtinger D, Plattner DA (2001) Chem Eur J 7:416

    Article  Google Scholar 

  68. de Bruin B, Peters TPJ, Wilting JBM, Thewissen S, Smits JMM, Gal AW (2002) Eur J Inorg Chem 2671

    Google Scholar 

  69. Vigalok A, Shimon LJW, Milstein D (1996) Chem Commun 1673

    Google Scholar 

  70. Day VW, Klemperer WG, Lockedge SP, Main DJ (1990) J Am Chem Soc 112:2031

    Article  CAS  Google Scholar 

  71. Tejel C, Ciriano MA, Sola E, del Río MP, Ríos-Moreno G, Lahoz FJ, Oro LA (2005) Angew Chem Int Ed 44:3267

    Article  CAS  Google Scholar 

  72. de Bruin B, Brands JA, Donners JJJM, Donners MPJ, de Gelder R, Smits JMM, Gal AW, Spek AL (1999) Chem Eur J 5:2921

    Article  Google Scholar 

  73. Farrissey WJ, Perry SH, Stehling FC, Chamberlain NF (1964) Tetrahedron Lett 48:3635

    Article  Google Scholar 

  74. Day VW, Eberspacher TA, Klemperer WG, Zhong B (1994) J Am Chem Soc 116:3119

    Article  CAS  Google Scholar 

  75. Hetterscheid DGH, de Bruin B, Smits JMM, Gal AW (2003) Organometallics 22:3022

    Article  CAS  Google Scholar 

  76. Hetterscheid DGH, Bens M, de Bruin B (2005) Dalton Trans 979

    Google Scholar 

  77. de Bruin, Peters TPJ, Thewissen S, Blok ANJ, Wilting JBM, de Gelder R, Smits JMM, Gal AW (2002) Angew Chem Int Ed 41:2135

    Article  Google Scholar 

  78. Hetterscheid DGH, Kaiser J, Reijerse E, Peters TJP, Thewissen S, Blok ANJ, Smits JMM, de Gelder R, de Bruin B (2005) J Am Chem Soc 127:1895

    Article  CAS  Google Scholar 

  79. de Bruin B, Boerakker MJ, Donners JJJM, Christiaans BEC, Schlebos PPJ, de Gelder R, Smits JMM, Spek AL, Gal AW (1997) Angew Chem Int Ed 36:2064

    Article  Google Scholar 

  80. de Bruin B, Boerakker M J, Verhagen JAW, de Gelder R, Smits JMM, Gal AW (2000) Chem Eur J 6:298

    Article  Google Scholar 

  81. Nishioka T, Onishi Y, Nakajo K, Guo-Xin J, Tanaka R, Kinoshita I (2005) Dalton Trans 2130

    Google Scholar 

  82. Flood TC, Iimura M, Perotti JM, Rheingold AL, Concolino TE (2000) Chem Commun 1681

    Google Scholar 

  83. Sciarone T, Hoogboom J, Schlebos PPJ, Budzelaar PHM, de Gelder R, Smits JMM, Gal AW (2002) Eur J Inorg Chem 457

    Google Scholar 

  84. Krom M, Coumans RGE, Smits JMM, Gal AW (2002) Angew Chem Int Ed 41:575

    Article  CAS  Google Scholar 

  85. Calhorda MJ, Galvão AM, Ünalerogly C, Zlota AA, Frolow F, Milstein D (1993) Organometallics 12:3316

    Article  CAS  Google Scholar 

  86. Milstein D (1982) J Am Chem Soc 124:5227

    Article  Google Scholar 

  87. Haarman HF, Bregman FR, van Leeuwen PWNM, Vrieze K (1997) Organometallics 16:979

    Article  CAS  Google Scholar 

  88. Takahashi Y, Hashimoto M, Hikichi S, Moro-oka Y, Akita M (2004) Inorg Chim Acta 357:1711

    Article  CAS  Google Scholar 

  89. Takahashi Y, Hashimoto M, Hikichi S, Akita M, Moro-oka Y (1999) Angew Chem Int Ed 38:3074

    Article  CAS  Google Scholar 

  90. Ahijado M, Braun T, Noveski D, Kocher N, Neumann B, Stalke D, Stammler H-G (2005) Angew Chem Int Ed 44:6947

    Article  CAS  Google Scholar 

  91. Hay-Motherwell RS, Wilkinson G, Hussain-Bates B, Hursthouse MB (1992) J Chem Soc Dalton Trans 3477

    Google Scholar 

  92. Jacobi BG, Laitar DS, Pu L, Wargocki MF, DiPascuale AG, Fortner KC, Schuck SM, Brown SN (2002) Inorg Chem 41:4815

    Article  CAS  Google Scholar 

  93. Lemma K, Bakac A (2004) Inorg Chem 43:4505

    Article  CAS  Google Scholar 

  94. Budzelaar PHM, Blok ANJ (2004) Eur J Inorg Chem 2385

    Google Scholar 

Download references

Acknowledgments

We are grateful to the Spanish Ministry of Education and Science (MEC/FEDER) and the Government of Aragón (DGA) for generous financial support (projects CTQ2005-06807/BQU) and (PIP019/2005), respectively.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Cristina Tejel .

Editor information

Franc Meyer Christian Limberg

Rights and permissions

Reprints and permissions

Copyright information

© 2006 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Tejel, C., Ciriano, M.A. (2006). Catalysis and Organometallic Chemistry of Rhodium and Iridium in the Oxidation of Organic Substrates. In: Meyer, F., Limberg, C. (eds) Organometallic Oxidation Catalysis. Topics in Organometallic Chemistry, vol 22. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_045

Download citation

Publish with us

Policies and ethics