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Recent Advances in Alkene Hydroformylation

  • Bernhard Breit
Chapter
Part of the Topics in Current Chemistry book series (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.

Keywords

Vinyl Acetate Rhodium Catalyst Terminal Alkene Zinc Porphyrin Internal Alkene 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Roelen O (1944) Chem Abstr 38:550 (Chemische Verwertungsgesellschaft, mbH Oberhausen, (1938/1952) DE Patent 849584) Google Scholar
  2. 2.
    Weissermel K, Arpe HJ (2003) Industrial organic chemistry. VCH, Weinheim, p 127 CrossRefGoogle Scholar
  3. 3.
    Wiese KD, Obst D (2006) Top Organomet Chem 18:1–33 CrossRefGoogle Scholar
  4. 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. 5.
    Breit B, Seiche W (2001) Synthesis p 1 Google Scholar
  6. 6.
    Breit B (2003) Acc Chem Res 36:264 CrossRefGoogle Scholar
  7. 7.
    Trost BM (1991) Science 254:1471 CrossRefGoogle Scholar
  8. 8.
    Trost BM (1995) Angew Chem Int Ed Engl 34:259 CrossRefGoogle Scholar
  9. 9.
    Eilbracht P, Schmidt AM (2006) Top Organomet Chem 18:65–95 CrossRefGoogle Scholar
  10. 10.
    van Leeuwen PWNM, Claver C (2000) Rhodium catalyzed hydroformylation. Kluwer, Dordrecht Google Scholar
  11. 11.
    Claver C, Diéguez M, Pamiès O, Castillón S (2006) Top Organomet Chem 18:35–64 CrossRefGoogle Scholar
  12. 12.
    Nozaki K, Ojima I (2000) Asymmetric carbonylation. In: Ojima I (ed) Catalytic asymmetric synthesis. Wiley-VCH, New York, p 429 CrossRefGoogle Scholar
  13. 13.
    Beller M, Seayad J, Tillack A, Jiao H (2004) Angew Chem Int Ed Engl 43:3368 CrossRefGoogle Scholar
  14. 14.
    Adams DJ, Cole-Hamilton DJ, Hope EG, Pogorzelec PJ, Stuart AM (2004) J Organomet Chem 689:1413 CrossRefGoogle Scholar
  15. 15.
    Bohnen HW, Cornils B (2007) Adv Catal 47:1–64 CrossRefGoogle Scholar
  16. 16.
    Cornils B, Herrmann WA (1998) Aqueous-phase organometallic catalysis—concepts and applications. Wiley-VCH, Weinheim Google Scholar
  17. 17.
    Ojima I, Tsai CY, Tzamarioudaki M, Bonafoux D (2000) Org React 56:1 Google Scholar
  18. 18.
    Torrent M, Solà M, Frenking G (2000) Chem Rev 100:439 CrossRefGoogle Scholar
  19. 19.
    van Leeuwen PWNM, Kamer PCJ, Reek JNH, Dierkes P (2000) Chem Rev 100:274 CrossRefGoogle Scholar
  20. 20.
    Beller M, Cornils B, Frohning CD, Kohlpaintner CW (1995) J Mol Catal A Chem 104:17 CrossRefGoogle Scholar
  21. 21.
    Ojima I, Eguchi M, Tzamarioudaki M (1995) Hydroformylation. In: Abel EW, Stone FGA, Wilkinson G (eds) Comprehensive organometallic chemistry. Elsevier, Oxford, p 9 CrossRefGoogle Scholar
  22. 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 CrossRefGoogle Scholar
  23. 23.
    Diéguez M, Pàmies O, Claver C (2004) Tetrahedron Asymmetry 15:2113 CrossRefGoogle Scholar
  24. 24.
    Kalck P, Peres Y, Jenck J (1991) Adv Organomet Chem 32:121 CrossRefGoogle Scholar
  25. 25.
    Agbossou F, Carpentier JF, Mortreux A (1995) Chem Rev 95:2485 CrossRefGoogle Scholar
  26. 26.
    Gladiali S, Bayon JC, Claver C (1995) Tetrahedron Asymmetry 6:1453 CrossRefGoogle Scholar
  27. 27.
    Breit B (2007) Directed Rhodium Catalyzed Hydroformylation of Alkenes. Top Organomet Chem, published online Google Scholar
  28. 28.
    Breit B (2005) Angew Chem Int Ed 44:6816 CrossRefGoogle Scholar
  29. 29.
    Evans DA, Osborn JA, Wilkinson G (1968) J Chem Soc A 3133 Google Scholar
  30. 30.
    Jongsma T, Challa G, van Leeuwen PWNM (1991) J Organomet Chem 421:121 CrossRefGoogle Scholar
  31. 31.
    Selent D, Wiese KD, Röttger D, Börner A (2000) Angew Chem Int Ed 39:1639 CrossRefGoogle Scholar
  32. 32.
    Breit B, Winde R, Mackewitz T, Paciello R, Harms K (2001) Chem Eur J 7:3106 CrossRefGoogle Scholar
  33. 33.
    Breit B (1999) J Mol Catal A 143:143 CrossRefGoogle Scholar
  34. 34.
    Breit B, Winde R, Harms K (1997) J Chem Soc Perkin Trans 1:2681 CrossRefGoogle Scholar
  35. 35.
    Breit B (1996) J Chem Soc Chem Commun p 2071 Google Scholar
  36. 36.
    Breit B, Fuchs E (2004) Chem Commun p 694 Google Scholar
  37. 37.
    Piechaczyk O, Doux M, Ricard L, le Floch P (2005) Organometallics 24:1204 CrossRefGoogle Scholar
  38. 38.
    Fuchs E, Keller M, Breit B (2006) Chem Eur J 12:6930 CrossRefGoogle Scholar
  39. 39.
    Keulemans AIM, Kwantes A, van Bavel T (1948) Recl Trav Chim Pays Bas 67:298 CrossRefGoogle Scholar
  40. 40.
    García L, Claver C, Diéguez M, Masdeu-Bultó AM (2006) Chem Commun p 191 Google Scholar
  41. 41.
    Clarke ML, Roff GJ (2006) Chem Eur J 12:7978 CrossRefGoogle Scholar
  42. 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. 43.
    Gee V, Orpen AG, Phetmung H, Pringle PG, Pugh RI (1999) Chem Commun p 901 Google Scholar
  44. 44.
    Pugh RI, Pringle PG, Drent E (2001) Chem Commun p 1476 Google Scholar
  45. 45.
    Reetz MT, Li X (2005) Angew Chem Int Ed 44:2962 CrossRefGoogle Scholar
  46. 46.
    Dong Y, Busacca CA (1997) J Org Chem 62:6464 CrossRefGoogle Scholar
  47. 47.
    Keränen MD, Eilbracht P (2004) Org Biomol Chem 2:1688 CrossRefGoogle Scholar
  48. 48.
    Keränen MD, Kot K, Hollmann C, Eilbracht P (2004) Org Biomol Chem 2:3379 CrossRefGoogle Scholar
  49. 49.
    Devon TJ, Phillips GW, Puckette TA, Stavinoha JL, Vanderbilt JJ (1987) US Patent 4694109 Google Scholar
  50. 50.
    Casey CP, Whiteker GT, Melville MG, Petrovich LM, Gavey JA, Powell DR (1992) J Am Chem Soc 114:5535 CrossRefGoogle Scholar
  51. 51.
    Billig E, Abatjoglou AG, Bryant DR (1988) US Patent 4769498 Google Scholar
  52. 52.
    Cunny GD, Buchwald SL (1993) J Am Chem 114:5535 Google Scholar
  53. 53.
    Kranenburg M, van der Burgt YEM, Kamer PCJ, van Leeuwen PWNM, Goubitz K, Fraanje J (1995) Organometallics 14:3081 CrossRefGoogle Scholar
  54. 54.
    Sémeril D, Jeunesse C, Matt D, Toupet L (2006) Angew Chem Int Ed 45:5810 CrossRefGoogle Scholar
  55. 55.
    Keck GE, Truong AP (2005) Org Lett 7:2149 CrossRefGoogle Scholar
  56. 56.
    Dixon DJ, Horan RAJ, Monck NJT (2004) Org Lett 6:4423 CrossRefGoogle Scholar
  57. 57.
    Petricci E, Mann A, Schoenfelder A, Rota A, Taddei M (2006) Org Lett 8:3725 CrossRefGoogle Scholar
  58. 58.
    Ahmed M, Seayad AM, Jackstell R, Beller M (2003) Angew Chem Int Ed 42:5615 CrossRefGoogle Scholar
  59. 59.
    Ahmed M, Seayad AM, Jackstell R, Beller M (2003) J Am Chem Soc 125:1031 CrossRefGoogle Scholar
  60. 60.
    Ahmed M, Bronger RPJ, Jackstell R, Kamer PCJ, van Leeuwen PWNM, Beller M (2006) Chem Eur J 12:8979 CrossRefGoogle Scholar
  61. 61.
    Schmidt AM, Eilbracht P (2005) Org Biomol Chem 3:2333 CrossRefGoogle Scholar
  62. 62.
    Schmidt AM, Eilbracht P (2005) J Org Chem 70:5528 CrossRefGoogle Scholar
  63. 63.
    Köhling P, Schmidt AM, Eilbracht P (2003) Org Lett 5:3213 CrossRefGoogle Scholar
  64. 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. 65.
    Sakai N, Mano S, Nozaki K, Takaya H (1993) J Am Chem Soc 115:7033 CrossRefGoogle Scholar
  66. 66.
    Nozaki K, Sakai N, Nanno T, Higashijima T, Mano S, Horiuchi T, Takaya H (1997) J Am Chem Soc 119:4413 CrossRefGoogle Scholar
  67. 67.
    Nozaki K, Itoi Y, Shibahara F, Shirakawa E, Ohta T, Takaya H, Hiyama T (1998) J Am Chem Soc 120:4051 CrossRefGoogle Scholar
  68. 68.
    Nakano K, Tanaka R, Nozaki K (2006) Helv Chim Acta 89:1681 CrossRefGoogle Scholar
  69. 69.
    Yan Y, Zhang X (2006) J Am Chem Soc 128:7198 CrossRefGoogle Scholar
  70. 70.
    Axtell AT, Klosin J, Abboud KA (2006) Organometallics 25:5003 CrossRefGoogle Scholar
  71. 71.
    Axtell AT, Cobley CJ, Klosin J, Whiteker GT, Zanotti-Gerosa A, Abboud KA (2005) Angew Chem Int Ed 44:5834 CrossRefGoogle Scholar
  72. 72.
    Clarkson GJ, Ansell JR, Cole-Hamilton DJ, Pogorzelec PJ, Whittell J, Wills M (2004) Tetrahedron Asymmetry 15:1787 CrossRefGoogle Scholar
  73. 73.
    Clark TP, Landis CR, Freed SL, Klosin J, Abboud KA (2005) J Am Chem Soc 127:5040 CrossRefGoogle Scholar
  74. 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 CrossRefGoogle Scholar
  75. 75.
    Liu P, Jacobsen EN (2001) J Am Chem Soc 123:10773 Google Scholar
  76. 76.
    Breit B (1996) Angew Chem Int Ed Engl 35:2835 CrossRefGoogle Scholar
  77. 77.
    Breit B (1997) Liebigs Ann Recl 1841 Google Scholar
  78. 78.
    Breit B, Heckmann G, Zahn SK (2003) Chem Eur J 9:425 CrossRefGoogle Scholar
  79. 79.
    Breit B, Dauber M, Harms K (1999) Chem Eur J 5:2819 CrossRefGoogle Scholar
  80. 80.
    Breit B, Demel P, Gebert A (2004) Chem Commun p 114 Google Scholar
  81. 81.
    Breit B (1997) Chem Commun p 591 Google Scholar
  82. 82.
    Breit B (1998) Eur J Org Chem 6:1123 CrossRefGoogle Scholar
  83. 83.
    Breit B, Breuninger D (2004) J Am Chem Soc p 10244 Google Scholar
  84. 84.
    Breit B, Breuninger D (2005) Synthesis p 2782 Google Scholar
  85. 85.
    Breit B, Breuninger D (2005) Eur J Org Chem p 3916 Google Scholar
  86. 86.
    Breit B, Breuninger D (2005) Eur J Org Chem p 3930 Google Scholar
  87. 87.
    Breit B (2005) Angew Chem Int Ed 44:6816 CrossRefGoogle Scholar
  88. 88.
    Breit B, Seiche W (2006) Pure Appl Chem 78:249 CrossRefGoogle Scholar
  89. 89.
    Breit B, Seiche W (2003) J Am Chem Soc 125:6608 CrossRefGoogle Scholar
  90. 90.
    Seiche W, Schuschkowski A, Breit B (2005) Adv Synth Catal 347:1488 CrossRefGoogle Scholar
  91. 91.
    Breit B, Seiche W (2005) Angew Chem Int Ed 44:1640 CrossRefGoogle Scholar
  92. 92.
    Waloch C, Wieland J, Keller M, Breit B (2007) Angew Chem Int Ed 46:3037 CrossRefGoogle Scholar
  93. 93.
    Slagt VF, van Leeuwen PWNM, Reek JNH (2003) Chem Commun p 2474 Google Scholar
  94. 94.
    Slagt VF, van Leeuwen PWNM, Reek JNH (2003) Angew Chem Int Ed 42:5619 CrossRefGoogle Scholar
  95. 95.
    Kuli M, Solter T, van Leeuwen PWNM, Reek JNH (2006) J Am Chem Soc 128:11344 CrossRefGoogle Scholar
  96. 96.
    Slagt VF, Kamer PCJ, van Leeuwen PWNM, Reek JNH (2004) J Am Chem Soc 126:1526 CrossRefGoogle Scholar
  97. 97.
    Slagt VF, Reek JNH, Kamer PCJ, van Leeuwen PWNM (2001) Angew Chem Int Ed 40:4271 CrossRefGoogle Scholar
  98. 98.
    Kuil M, Goudriaan PE, van Leeuwen PWNM, Reek JNH (2006) Chem Commun p 4679 Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2007

Authors and Affiliations

  1. 1.Institut für Organische Chemie und BiochemieAlbert-Ludwigs Universität FreiburgFreiburg im BreisgauGermany

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