Skip to main content
SpringerLink
Log in

Recent Advances in Alkene Hydroformylation

  • Chapter
  • First Online:
Metal Catalyzed Reductive C–C Bond Formation

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 279))

Abstract

Recent advances in synthetic aspects of the rhodium-catalyzed hydroformylation of alkenes are reviewed. Emphasis is given to practical improvements, efficient new catalysts for regioselective and enantioselective hydroformylation, and to applications of the reaction in organic synthesis. Furthermore, new developments in directed hydroformylation are covered as well as new approaches toward efficient hydroformylation catalysts employing the concept of self-assembly.

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 299.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 379.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 379.99
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. Roelen O (1944) Chem Abstr 38:550 (Chemische Verwertungsgesellschaft, mbH Oberhausen, (1938/1952) DE Patent 849584)

    Google Scholar 

  2. Weissermel K, Arpe HJ (2003) Industrial organic chemistry. VCH, Weinheim, p 127

    Book  Google Scholar 

  3. Wiese KD, Obst D (2006) Top Organomet Chem 18:1–33

    Article  CAS  Google Scholar 

  4. Breit B (2007) Aldehydes: synthesis by hydroformylation of alkenes. In: Brückner R (ed) Science of synthesis, vol 25. Thieme, Stuttgart, pp 277–317

    Google Scholar 

  5. Breit B, Seiche W (2001) Synthesis p 1

    Google Scholar 

  6. Breit B (2003) Acc Chem Res 36:264

    Article  CAS  Google Scholar 

  7. Trost BM (1991) Science 254:1471

    Article  CAS  Google Scholar 

  8. Trost BM (1995) Angew Chem Int Ed Engl 34:259

    Article  CAS  Google Scholar 

  9. Eilbracht P, Schmidt AM (2006) Top Organomet Chem 18:65–95

    Article  CAS  Google Scholar 

  10. van Leeuwen PWNM, Claver C (2000) Rhodium catalyzed hydroformylation. Kluwer, Dordrecht

    Google Scholar 

  11. Claver C, Diéguez M, Pamiès O, Castillón S (2006) Top Organomet Chem 18:35–64

    Article  CAS  Google Scholar 

  12. Nozaki K, Ojima I (2000) Asymmetric carbonylation. In: Ojima I (ed) Catalytic asymmetric synthesis. Wiley-VCH, New York, p 429

    Chapter  Google Scholar 

  13. Beller M, Seayad J, Tillack A, Jiao H (2004) Angew Chem Int Ed Engl 43:3368

    Article  CAS  Google Scholar 

  14. Adams DJ, Cole-Hamilton DJ, Hope EG, Pogorzelec PJ, Stuart AM (2004) J Organomet Chem 689:1413

    Article  CAS  Google Scholar 

  15. Bohnen HW, Cornils B (2007) Adv Catal 47:1–64

    Article  Google Scholar 

  16. Cornils B, Herrmann WA (1998) Aqueous-phase organometallic catalysis—concepts and applications. Wiley-VCH, Weinheim

    Google Scholar 

  17. Ojima I, Tsai CY, Tzamarioudaki M, Bonafoux D (2000) Org React 56:1

    CAS  Google Scholar 

  18. Torrent M, Solà M, Frenking G (2000) Chem Rev 100:439

    Article  CAS  Google Scholar 

  19. van Leeuwen PWNM, Kamer PCJ, Reek JNH, Dierkes P (2000) Chem Rev 100:274

    Article  CAS  Google Scholar 

  20. Beller M, Cornils B, Frohning CD, Kohlpaintner CW (1995) J Mol Catal A Chem 104:17

    Article  CAS  Google Scholar 

  21. Ojima I, Eguchi M, Tzamarioudaki M (1995) Hydroformylation. In: Abel EW, Stone FGA, Wilkinson G (eds) Comprehensive organometallic chemistry. Elsevier, Oxford, p 9

    Chapter  Google Scholar 

  22. Stille JK (1991) Hydroformylation and related additions of carbon monoxide to alkenes and alkynes. In: Trost BM, Fleming I, Paquette LA (eds) Comprehensive organic synthesis. Pergamon, Oxford, p 913

    Chapter  Google Scholar 

  23. Diéguez M, Pàmies O, Claver C (2004) Tetrahedron Asymmetry 15:2113

    Article  CAS  Google Scholar 

  24. Kalck P, Peres Y, Jenck J (1991) Adv Organomet Chem 32:121

    Article  CAS  Google Scholar 

  25. Agbossou F, Carpentier JF, Mortreux A (1995) Chem Rev 95:2485

    Article  CAS  Google Scholar 

  26. Gladiali S, Bayon JC, Claver C (1995) Tetrahedron Asymmetry 6:1453

    Article  CAS  Google Scholar 

  27. Breit B (2007) Directed Rhodium Catalyzed Hydroformylation of Alkenes. Top Organomet Chem, published online

    Google Scholar 

  28. Breit B (2005) Angew Chem Int Ed 44:6816

    Article  CAS  Google Scholar 

  29. Evans DA, Osborn JA, Wilkinson G (1968) J Chem Soc A 3133

    Google Scholar 

  30. Jongsma T, Challa G, van Leeuwen PWNM (1991) J Organomet Chem 421:121

    Article  CAS  Google Scholar 

  31. Selent D, Wiese KD, Röttger D, Börner A (2000) Angew Chem Int Ed 39:1639

    Article  CAS  Google Scholar 

  32. Breit B, Winde R, Mackewitz T, Paciello R, Harms K (2001) Chem Eur J 7:3106

    Article  CAS  Google Scholar 

  33. Breit B (1999) J Mol Catal A 143:143

    Article  CAS  Google Scholar 

  34. Breit B, Winde R, Harms K (1997) J Chem Soc Perkin Trans 1:2681

    Article  Google Scholar 

  35. Breit B (1996) J Chem Soc Chem Commun p 2071

    Google Scholar 

  36. Breit B, Fuchs E (2004) Chem Commun p 694

    Google Scholar 

  37. Piechaczyk O, Doux M, Ricard L, le Floch P (2005) Organometallics 24:1204

    Article  CAS  Google Scholar 

  38. Fuchs E, Keller M, Breit B (2006) Chem Eur J 12:6930

    Article  CAS  Google Scholar 

  39. Keulemans AIM, Kwantes A, van Bavel T (1948) Recl Trav Chim Pays Bas 67:298

    Article  CAS  Google Scholar 

  40. García L, Claver C, Diéguez M, Masdeu-Bultó AM (2006) Chem Commun p 191

    Google Scholar 

  41. Clarke ML, Roff GJ (2006) Chem Eur J 12:7978

    Article  CAS  Google Scholar 

  42. Baber RA, Clarke ML, Heslop K, Marr A, Orpen AG, Pringle PG, Ward AM, Zambrano-Williams DA (2005) Dalton Trans p 1079

    Google Scholar 

  43. Gee V, Orpen AG, Phetmung H, Pringle PG, Pugh RI (1999) Chem Commun p 901

    Google Scholar 

  44. Pugh RI, Pringle PG, Drent E (2001) Chem Commun p 1476

    Google Scholar 

  45. Reetz MT, Li X (2005) Angew Chem Int Ed 44:2962

    Article  CAS  Google Scholar 

  46. Dong Y, Busacca CA (1997) J Org Chem 62:6464

    Article  CAS  Google Scholar 

  47. Keränen MD, Eilbracht P (2004) Org Biomol Chem 2:1688

    Article  CAS  Google Scholar 

  48. Keränen MD, Kot K, Hollmann C, Eilbracht P (2004) Org Biomol Chem 2:3379

    Article  Google Scholar 

  49. Devon TJ, Phillips GW, Puckette TA, Stavinoha JL, Vanderbilt JJ (1987) US Patent 4694109

    Google Scholar 

  50. Casey CP, Whiteker GT, Melville MG, Petrovich LM, Gavey JA, Powell DR (1992) J Am Chem Soc 114:5535

    Article  CAS  Google Scholar 

  51. Billig E, Abatjoglou AG, Bryant DR (1988) US Patent 4769498

    Google Scholar 

  52. Cunny GD, Buchwald SL (1993) J Am Chem 114:5535

    Google Scholar 

  53. Kranenburg M, van der Burgt YEM, Kamer PCJ, van Leeuwen PWNM, Goubitz K, Fraanje J (1995) Organometallics 14:3081

    Article  CAS  Google Scholar 

  54. Sémeril D, Jeunesse C, Matt D, Toupet L (2006) Angew Chem Int Ed 45:5810

    Article  CAS  Google Scholar 

  55. Keck GE, Truong AP (2005) Org Lett 7:2149

    Article  CAS  Google Scholar 

  56. Dixon DJ, Horan RAJ, Monck NJT (2004) Org Lett 6:4423

    Article  CAS  Google Scholar 

  57. Petricci E, Mann A, Schoenfelder A, Rota A, Taddei M (2006) Org Lett 8:3725

    Article  CAS  Google Scholar 

  58. Ahmed M, Seayad AM, Jackstell R, Beller M (2003) Angew Chem Int Ed 42:5615

    Article  CAS  Google Scholar 

  59. Ahmed M, Seayad AM, Jackstell R, Beller M (2003) J Am Chem Soc 125:1031

    Article  CAS  Google Scholar 

  60. Ahmed M, Bronger RPJ, Jackstell R, Kamer PCJ, van Leeuwen PWNM, Beller M (2006) Chem Eur J 12:8979

    Article  CAS  Google Scholar 

  61. Schmidt AM, Eilbracht P (2005) Org Biomol Chem 3:2333

    Article  CAS  Google Scholar 

  62. Schmidt AM, Eilbracht P (2005) J Org Chem 70:5528

    Article  CAS  Google Scholar 

  63. Köhling P, Schmidt AM, Eilbracht P (2003) Org Lett 5:3213

    Article  CAS  Google Scholar 

  64. Rodriquez M, Bassarello C, Bifulco G, Gomez-Paloma L, Mann A, Marchetti M, Schoenfelder A, Taddei M (2005) Synlett p 1581

    Google Scholar 

  65. Sakai N, Mano S, Nozaki K, Takaya H (1993) J Am Chem Soc 115:7033

    Article  CAS  Google Scholar 

  66. Nozaki K, Sakai N, Nanno T, Higashijima T, Mano S, Horiuchi T, Takaya H (1997) J Am Chem Soc 119:4413

    Article  CAS  Google Scholar 

  67. Nozaki K, Itoi Y, Shibahara F, Shirakawa E, Ohta T, Takaya H, Hiyama T (1998) J Am Chem Soc 120:4051

    Article  CAS  Google Scholar 

  68. Nakano K, Tanaka R, Nozaki K (2006) Helv Chim Acta 89:1681

    Article  CAS  Google Scholar 

  69. Yan Y, Zhang X (2006) J Am Chem Soc 128:7198

    Article  CAS  Google Scholar 

  70. Axtell AT, Klosin J, Abboud KA (2006) Organometallics 25:5003

    Article  CAS  Google Scholar 

  71. Axtell AT, Cobley CJ, Klosin J, Whiteker GT, Zanotti-Gerosa A, Abboud KA (2005) Angew Chem Int Ed 44:5834

    Article  CAS  Google Scholar 

  72. Clarkson GJ, Ansell JR, Cole-Hamilton DJ, Pogorzelec PJ, Whittell J, Wills M (2004) Tetrahedron Asymmetry 15:1787

    Article  CAS  Google Scholar 

  73. Clark TP, Landis CR, Freed SL, Klosin J, Abboud KA (2005) J Am Chem Soc 127:5040

    Article  CAS  Google Scholar 

  74. Cobley CJ, Gardner K, Klosin J, Praquin C, Hill C, Whiteker GT, Zanotti-Gerosa A, Petersen JL, Abboud KA (2004) J Org Chem 69:4031

    Article  CAS  Google Scholar 

  75. Liu P, Jacobsen EN (2001) J Am Chem Soc 123:10773

    Google Scholar 

  76. Breit B (1996) Angew Chem Int Ed Engl 35:2835

    Article  CAS  Google Scholar 

  77. Breit B (1997) Liebigs Ann Recl 1841

    Google Scholar 

  78. Breit B, Heckmann G, Zahn SK (2003) Chem Eur J 9:425

    Article  CAS  Google Scholar 

  79. Breit B, Dauber M, Harms K (1999) Chem Eur J 5:2819

    Article  CAS  Google Scholar 

  80. Breit B, Demel P, Gebert A (2004) Chem Commun p 114

    Google Scholar 

  81. Breit B (1997) Chem Commun p 591

    Google Scholar 

  82. Breit B (1998) Eur J Org Chem 6:1123

    Article  Google Scholar 

  83. Breit B, Breuninger D (2004) J Am Chem Soc p 10244

    Google Scholar 

  84. Breit B, Breuninger D (2005) Synthesis p 2782

    Google Scholar 

  85. Breit B, Breuninger D (2005) Eur J Org Chem p 3916

    Google Scholar 

  86. Breit B, Breuninger D (2005) Eur J Org Chem p 3930

    Google Scholar 

  87. Breit B (2005) Angew Chem Int Ed 44:6816

    Article  CAS  Google Scholar 

  88. Breit B, Seiche W (2006) Pure Appl Chem 78:249

    Article  CAS  Google Scholar 

  89. Breit B, Seiche W (2003) J Am Chem Soc 125:6608

    Article  CAS  Google Scholar 

  90. Seiche W, Schuschkowski A, Breit B (2005) Adv Synth Catal 347:1488

    Article  CAS  Google Scholar 

  91. Breit B, Seiche W (2005) Angew Chem Int Ed 44:1640

    Article  CAS  Google Scholar 

  92. Waloch C, Wieland J, Keller M, Breit B (2007) Angew Chem Int Ed 46:3037

    Article  CAS  Google Scholar 

  93. Slagt VF, van Leeuwen PWNM, Reek JNH (2003) Chem Commun p 2474

    Google Scholar 

  94. Slagt VF, van Leeuwen PWNM, Reek JNH (2003) Angew Chem Int Ed 42:5619

    Article  CAS  Google Scholar 

  95. Kuli M, Solter T, van Leeuwen PWNM, Reek JNH (2006) J Am Chem Soc 128:11344

    Article  CAS  Google Scholar 

  96. Slagt VF, Kamer PCJ, van Leeuwen PWNM, Reek JNH (2004) J Am Chem Soc 126:1526

    Article  CAS  Google Scholar 

  97. Slagt VF, Reek JNH, Kamer PCJ, van Leeuwen PWNM (2001) Angew Chem Int Ed 40:4271

    Article  CAS  Google Scholar 

  98. Kuil M, Goudriaan PE, van Leeuwen PWNM, Reek JNH (2006) Chem Commun p 4679

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Organische Chemie und Biochemie, Albert-Ludwigs Universität Freiburg, Albertstr. 21, 79104, Freiburg im Breisgau, Germany

    Bernhard Breit

Authors
  1. Bernhard Breit
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Bernhard Breit .

Editor information

Michael J. Krische

Rights and permissions

Reprints and permissions

Copyright information

© 2007 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Breit, B. (2007). Recent Advances in Alkene Hydroformylation. In: Krische, M.J. (eds) Metal Catalyzed Reductive C–C Bond Formation. Topics in Current Chemistry, vol 279. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2007_136

Download citation

Publish with us

Policies and ethics

Search

Navigation