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Insertion and β-Hydrogen Transfer at Aluminium

  • Peter H. M. Budzelaar
  • Giovanni Talarico
Chapter
Part of the Structure and Bonding book series (STRUCTURE, volume 105)

Abstract

Insertion and elimination of C=X bonds are two fundamental steps of organometallic chemistry. In aluminium chemistry, these reaction steps are important in olefin oligomerization and possibly polymerization, as well as in the reaction of carbonyl compounds with aluminium alkyls. The general importance of a third fundamental step, direct β-hydrogen transfer from an aluminium-bound group to a substrate, has not been recognized as widely, despite the fact that it is the key step in the reduction of ketones by alcohols (Meerwein-Pondorf-Verley reduction) and by aluminium alkyls bearing β-hydrogens. In this review we will combine experimental and theoretical results to illustrate how the delicate balance between these three reaction types determines much of the chemistry of organoaluminium compounds. Such an understanding may create new opportunities for ligand design.

Keywords

Chain Transfer Aluminium Alkoxide Aluminium Alkyl Organomagnesium Compound Insertion Barrier 
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.
    Ziegler K, Gellert H (1950) Liebigs Ann Chem 567: 195CrossRefGoogle Scholar
  2. 2.
    Mole T, Jeffery EA (1972) Organoaluminium Compounds, Elsevier, AmsterdamGoogle Scholar
  3. 3.
    Ziegler K, Holzkamp E, Breil H, Martin H (1955) Angew Chem 57: 541CrossRefGoogle Scholar
  4. 4.
    Margl P, Deng L, Ziegler T (1999) J Am Chem Soc 121: 154CrossRefGoogle Scholar
  5. 5.
    Talarico G, Budzelaar PHM, Gal AW (2000) J Comp Chem 21: 398CrossRefGoogle Scholar
  6. 6.
    Talarico G, Budzelaar PHM, Barone V, Adamo C (2000) Chem Phys Lett 329: 99CrossRefGoogle Scholar
  7. 7.
    Talarico G, Budzelaar PHM (2000) Organometallics 19: 5691CrossRefGoogle Scholar
  8. 8.
    Talarico G, Busico V, Budzelaar PHM (2001) Organometallics 20: 4721CrossRefGoogle Scholar
  9. 9.
    Martin H, Bretinger H (1992) Makromol Chem 193: 1283CrossRefGoogle Scholar
  10. 10.
    Coles MP, Jordan RF (1997) J Am Chem Soc 119: 8125CrossRefGoogle Scholar
  11. 11.
    Ihara E, Young Jr VG, Jordan RF (1998) J Am Chem Soc 120: 8277CrossRefGoogle Scholar
  12. 12.
    Bruce M, Gibson VC, Redshaw C, Solan GA, White AJP, Williams DJ (1998) Chem Commun 2523Google Scholar
  13. 13.
    Kim JS, Wojcinski II LM, Liu S, Sworen JC, Sen A (2000) J Am Chem Soc 122: 5668CrossRefGoogle Scholar
  14. 14.
    Dagorne S, Guzei IA, Coles MP, Jordan RF (2000) J Am Chem Soc 122: 274CrossRefGoogle Scholar
  15. 15.
    Korolev AV, Ihara E, Guzei IA, Young Jr VG, Jordan RF (2001) J Am Chem Soc 123: 8291CrossRefGoogle Scholar
  16. 16.
    Hauske JR (1991) Organoaluminum Reagents. In: Trost BM, Fleming I (eds) Comprehensive Organic Synthesis. Pergamon, Oxford, Sect. 1.3Google Scholar
  17. 18.
    Maruoka K, Yamamoto H (1988) Tetrahedron 44: 5001CrossRefGoogle Scholar
  18. 19.
    Eisch JJ (1982) Aluminum. In: Wilkinson G, Stone FGA, Abel EW (eds) Comprehensive Organometallic Chemistry, Vol 1. Pergamon, Oxford, Chap. 10Google Scholar
  19. 20.
    Eisch JJ (1995) Aluminum. In: Abel EW, Stone FGA, Wilkinson G (eds) Comprehensive Organometallic Chemistry II, Vol 1. Pergamon, Oxford, Chap. 10Google Scholar
  20. 21.
    Eisch JJ (1995) Aluminum. In: Abel EW, Stone FGA, Wilkinson G (eds) Comprehensive Organometallic Chemistry II, Vol 11. Pergamon, Oxford, Chap. 6Google Scholar
  21. 22.
    De Graauw CF, Peters JA, Van Bekkum H, Huskens J (1994) Synthesis 1007Google Scholar
  22. 23.
    Egger KW (1972) J Chem Soc Faraday 168: 1017Google Scholar
  23. 24.
    Egger KW (1969) J Am Chem Soc 91: 2867CrossRefGoogle Scholar
  24. 25.
    Egger KW (1969) Int J Chem Kinetics 1: 459CrossRefGoogle Scholar
  25. 26.
    Sakai S (1991) J Phys Chem 95: 175CrossRefGoogle Scholar
  26. 27.
    Bundens JW, Yudenfreund J, Francl MM (1999) Organometallics 18: 3913CrossRefGoogle Scholar
  27. 28.
    Reinhold M, McGrady JE, Meier R (1999) J Chem Soc Dalton Trans 484Google Scholar
  28. 29.
    Cavallo L, personal communicationGoogle Scholar
  29. 30.
    Wilke G (1995). In: Fink G, Mülhaupt R, Brintzinger HH (eds) Ziegler Catalysts. Springer-Verlag, Berlin, p 3Google Scholar
  30. 31.
    March J (1977) Advanced Organic Chemistry, 2nd ed. McGraw-Hill, New York, pp 1037–1041Google Scholar
  31. 32.
    Houk KN, Li Y, Evanseck JD (1992) Angew Chem 104: 711CrossRefGoogle Scholar
  32. 34. (a)
    Small BL, Brookhart M, Bennett AMA (1998) J Am Chem Soc 120: 4049CrossRefGoogle Scholar
  33. 34. (b)
    Britovsek GJP, Gibson VC, Kimberley BS, Maddox PJ, McTavish SJ, Solan GA, White AJP, Williams DJ (1998) Chem Commun 849Google Scholar
  34. 34. (c)
    Small BL, Brookhart M (1998) J Am Chem Soc 120: 7143CrossRefGoogle Scholar
  35. 34. (d)
    Britovsek GJP, Bruce M, Gibson VC, Kimberley BS, Maddox PJ, Mastroianni S, McTavish SJ, Redshaw C, Solan GA, Strömberg S, White AJP, Williams DJ (1999) J Am Chem Soc 121: 8728CrossRefGoogle Scholar
  36. 34. (e)
    Britovsek GJP, Mastroianni S, Solan GA, Baugh SPD, Redshaw C, Gibson VC, White AJP, Williams DJ, Elsegood MRJ (2000) Chem Eur J 6: 2221CrossRefGoogle Scholar
  37. 35.
    Meier RJ, Koglin E (2001) J Phys Chem A 105: 3867CrossRefGoogle Scholar
  38. 36.
    Budzelaar PHM, Talarico G. ACS Symposium Series 822 (2002) Chap. 10, p 142CrossRefGoogle Scholar
  39. 37.
    Talarico G, Budzelaar PHM (2001) Organometallics 21: 34CrossRefGoogle Scholar
  40. 38.
    Coles MP, Swenson DC, Jordan RF (1998) Organometallics 17: 4042CrossRefGoogle Scholar
  41. 39.
    Coles MP, Swenson DC, Jordan RF, Young Jr VG (1997) Organometallics 16: 5183CrossRefGoogle Scholar
  42. 40.
    Dagorne S, Jordan RF, Young Jr VG (1999) Organometallics 18: 4619CrossRefGoogle Scholar
  43. 41.
    Korolev AV, Guzei IA, Jordan RF (1999) J Am Chem Soc 121: 11605CrossRefGoogle Scholar
  44. 42.
    Radzewich CE, Coles MP, Jordan RF (1998) J Am Chem Soc 120: 9384CrossRefGoogle Scholar
  45. 43.
    Radzewich CE, Guzei IA, Jordan RF (1999) J Am Chem Soc 121: 8673CrossRefGoogle Scholar
  46. 44.
    Aeilts SL, Coles MP, Swenson DC, Jordan RF (1998) Organometallics 17: 3265CrossRefGoogle Scholar
  47. 45.
    Aparna K, McDonald R, Ferguson M, Cavell RG (1999) Organometallics 18: 4241CrossRefGoogle Scholar
  48. 46.
    Chen EY-X, Marks TJ (2000) Chem Rev 100: 1391CrossRefGoogle Scholar
  49. 48.
    Zhou Y, Richeson DS (1996) Inorg Chem 35: 1423CrossRefGoogle Scholar
  50. 49.
    McGrady GS, Turner JFC, Ibberson RM, Prager M (2000) Organometallics 19: 4398CrossRefGoogle Scholar
  51. 50.
    Neumann HM, Laemmle J, Ashby EC (1973) J Am Chem Soc 95: 2597CrossRefGoogle Scholar
  52. 51.
    Eisch JJ, Fichter KC (1984) J Org Chem 49: 4631CrossRefGoogle Scholar
  53. 52.
    Haubenstock H, Davidson EB (1963) J Org Chem 28: 2772CrossRefGoogle Scholar
  54. 53.
    Iguchi S, Nakai H, Hayashi M, Yamamoto H, Maruoka K (1981) Bull Chem Soc Jpn 54: 3033CrossRefGoogle Scholar
  55. 54.
    Haubenstock H (1990) Tetrahedron 46: 6633CrossRefGoogle Scholar
  56. 55.
    Meyer-Stork MA, Haag D, Scharf H-D (1997) J Chem Soc Perkin Trans 2 593Google Scholar
  57. 56.
    Meerwien H, Schmidt R (1925) Liebigs Ann Chem 444: 221CrossRefGoogle Scholar
  58. 57.
    Verley A (1925) Bull Soc Chim Fr 37: 537Google Scholar
  59. 58.
    Pondorf W (1926) Angew Chem 39: 138CrossRefGoogle Scholar
  60. 59.
    Oppenauer RV (1937) Recl Trav Chim Pays-Bas 56: 137Google Scholar
  61. 60.
    Doering WvE, Young RW (1950) J Am Chem Soc 72: 631CrossRefGoogle Scholar
  62. 61.
    Menicagli R, Giacomelli GP, Lardicci L (1973) J Organomet Chem 50: C15CrossRefGoogle Scholar
  63. 62.
    Xianming H, Kellogg RM (1996) Recl Trav Chim Pays-Bas 115: 410Google Scholar
  64. 63.
    Evans DA, Nelson SG, Gagné MR, Muci AR (1993) J Am Chem Soc 115: 9800CrossRefGoogle Scholar
  65. 64.
    Ishihara K, Hanaki N, Yamamoto H (1993) Synlett 127Google Scholar
  66. 65.
    Fujita M, Takarada Y, Sugimura T, Tai A (1997) Chem Commun 1631Google Scholar
  67. 66.
    Node M, Nishide K, Shigeta Y, Shiraki H, Obata K (2000) J Am Chem Soc 122: 1927CrossRefGoogle Scholar
  68. 67.
    Aremo N, Hase T (2001) Tetrahedron Lett 42: 3637CrossRefGoogle Scholar
  69. 68.
    Akamanchi KG, Varalakshmy NR (1995) Tetrahedron Lett 36: 3571CrossRefGoogle Scholar
  70. 69.
    Ko B-T, Wu C-C, Lin C-C (2000) Organometallics 19: 1864CrossRefGoogle Scholar
  71. 70.
    Ooi T, Miura T, Maruoka K (1998) Angew Chem Int Ed 37: 2347CrossRefGoogle Scholar
  72. 71.
    Ooi T, Itagaki Y, Miura T, Maruoka K (1999) Tetrahedron Lett 40: 2137CrossRefGoogle Scholar
  73. 72.
    Ashby EC (1988) Acc Chem Res 21: 414CrossRefGoogle Scholar
  74. 73.
    Lindsell WE (1982) Magnesium, Calcium, Strontium and Barium. In: Wilkinson G, Stone FGA, Abel EW (eds) Comprehensive Organometallic Chemistry, Vol 1. Pergamon, Oxford, Chap. 3Google Scholar
  75. 74.
    Bailey PJ, Coxall RA, Dick CM, Fabre S, Parsons S (2001) Organometallics 20: 798CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2003

Authors and Affiliations

  • Peter H. M. Budzelaar
    • 1
  • Giovanni Talarico
    • 2
  1. 1.Department of Inorganic ChemistryUniversity of NijmegenNijmegenThe Netherlands
  2. 2.Dipartimento di ChimicaUniversità degli Studi di Napoli “Federico II”NapoliItaly

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