Skip to main content
Log in

Homogeneous catalysis by gold

  • Published:
Gold Bulletin Aims and scope Submit manuscript

Abstract

A comprehensive overview in the field of homogeneous catalysis by gold is given and the basic principles are discussed. It is also highlighted where homogeneous gold catalysts are already superior to other catalysts and where future possibilities for advantageous use of homogeneous gold catalysts exist.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. A. Simmer,Arch. Pharm., 1907,244, 672–684

    Article  CAS  Google Scholar 

  2. H. Baggesgaard-Rasmussen, G. Espersen and J. Berger,Dansk Tidsskr. Farm. Suppl., 1956,2, 9–27

    CAS  Google Scholar 

  3. H. Schmidbaur,Naturw. Rdsch., 1995,48, 443–451

    Google Scholar 

  4. K. Tanaka,Solvent-free Organic Synthesis, Wiley-VCH, Weinheim, 2003

    Book  Google Scholar 

  5. W. Schwemberger and W. Gordon,Chem. Zentralbl., 1935,106, 514–514

    Google Scholar 

  6. P.G. Gassman, G.R. Meyer and F.J. Williams,J. Am. Chem. Soc., 1972,94, 7741–7748

    Article  Google Scholar 

  7. L.-U. Meyer and A. de Meijere,Tetrahedron Lett., 1976, 497-500

  8. F. Herrmann,Ber. Dtsch. Chem. Ges., 1905,38, 2813–2825

    Article  CAS  Google Scholar 

  9. F. Gasparrini, M. Giovannoli, D. Misiti, G. Natile and G. Palmieri,Tetrahedron, 1983,39, 3181–3184

    Article  CAS  Google Scholar 

  10. F. Gasparrini, M. Giovannoli, D. Misiti, G. Natile and G. Palmieri,Tetrahedron, 1984,40, 165–170

    Article  CAS  Google Scholar 

  11. F. Gasparrini, M. Giovannoli, D. Misiti, G. Natile and G. Palmieri,J. Org. Chem., 1990,55, 1323–1328

    Article  CAS  Google Scholar 

  12. E. Boring, Y.V. Geletii and C.L. Hill,J. Am. Chem. Soc., 2001,123, 1625–1635

    Article  CAS  Google Scholar 

  13. D.P. Riley,Inorg. Chem., 1983,22, 1965–1967

    Article  CAS  Google Scholar 

  14. D.P. Riley, M.R. Smith, P.E. Correa,J. Am. Chem. Soc., 1988,110, 177–180

    Article  CAS  Google Scholar 

  15. F. Gasparrini, M. Giovannoli, D. Misiti, G. Natile, G. Palmieri and L. Maresca,J. Am. Chem. Soc., 1993,115, 4401–4402

    Article  CAS  Google Scholar 

  16. F. Shi, Y. Deng, H. Yang and T. SiMa,J. Chem. Soc., Chem. Commun., 2001, 345–346

  17. F. Shi and Y. Deng,J. Chem. Soc., Chem. Commun., 2001, 443–444

  18. G.B. Shul'pin, A.E. Shilov and G. Süss-Fink,Tetrahedron Lett., 2001,42, 7253–7256

    Article  Google Scholar 

  19. J. Sundermeyer and C. Jost, DE 10041510 1999 [Chem. Abs., 2001,134, 280723]

    Google Scholar 

  20. A. von Baeyer and V. Villiger,Ber. Dtsch. Chem. Ges., 1899,32, 3622–3633

    Google Scholar 

  21. L.A. Levchenko, A.P. Sadkon, N.V. Lariontseva, E.M. Koldasheva, A.K. Shilova and A.E. Shilov,J. Inorg. Biochem., 2002, 88, 251–253

    Article  CAS  Google Scholar 

  22. Y. Ito, M. Sawamura and T. Hayashi,J. Am. Chem. Soc., 1986,108, 6405–6406

    Article  CAS  Google Scholar 

  23. M. Sawamura and Y. Ito,Chem. Rev., 1992,92, 857–871

    Article  CAS  Google Scholar 

  24. S.D. Pastor inEncyclopedia of Reagents for Organic Synthesis (Ed. L.A. Paquette), Vol. 1, Wiley, Chichester, 1995, 447–450

    Google Scholar 

  25. M. Sawamura and Y. Ito inCatalytic Asymmetric Synthesis (Ed. I. Ojima), First edition, VCH, 1993, 367–388; Second edition, Wiley-VCH, New York, 2000, 493–512

  26. X.-T. Zhou, Y.-R. Lin and L.-X. Dai,Tetrahedron Assym., 1999,10, 855–862

    Article  CAS  Google Scholar 

  27. D. Li, C.-M. Che, H.-L. Kwong and V.W.-W. Yam,J. Chem. Soc., Dalton Trans., 1992, 3325–3329

  28. S. Komiya, T. Sone, Y. Usui, M. Hirano and A. Fukuoka,Gold Bull., 1996,29, 131–136

    Article  CAS  Google Scholar 

  29. Q. Xu, Y. Imamura, M. Fujiwara and Y. Souma,J. Org. Chem., 1997,62, 1594–1598

    Article  CAS  Google Scholar 

  30. G. Wagner, W. Brickner,Ber. Dtsch. Chem. Ges., 1899,32, 2302–2325

    Article  CAS  Google Scholar 

  31. H. Meerwein,Liebigs Ann. Chem., 1918,417, 255–277

    Article  CAS  Google Scholar 

  32. G. Kaup,Top. Curr. Chem., 1988,146, 57–98

    Article  Google Scholar 

  33. H. Koch, W. Haaf,Angew. Chem., 1958,70, 311–311

    Google Scholar 

  34. A.S.K. Hashmi, L. Schwarz, J.-H. Choi and T.M. Frost,Angew. Chem., 2000,112, 2382–2385;Angew. Chem. Int. Ed., 2000,39, 2285–2288

    Article  Google Scholar 

  35. A.S.K. Hashmi,Angew. Chem., 2000,112, 3737–3740;Angew. Chem. Int. Ed., 2000,39, 3590–3593

    Article  Google Scholar 

  36. A. de Meijere,Angew. Chem., 1994,106, 2473–2506;Angew. Chem. Int. Ed., 1994,33, 2379–2411

    Article  Google Scholar 

  37. 37 For the recent description of gold hydride anions and a discussion of the problems with gold hydrides, see: X. Wang and L. Andrews,Angew. Chem., 2003,115, 5359–5364;Angew. Chem. Int. Ed., 2003,42, 5201–5206

    Article  Google Scholar 

  38. G. Dyker, E. Muth, A.S.K. Hashmi and L. Ding,Adv. Synth. Catal., 2003,345, 1247–1252

    Article  CAS  Google Scholar 

  39. A.S.K. Hashmi,Gold Bull., 2003,36, 3–9

    Article  CAS  Google Scholar 

  40. A.S.K. Hashmi, T.M. Frost and J.W. Bats,J. Am. Chem. Soc., 2000,122, 11553–11554

    Article  CAS  Google Scholar 

  41. A.S.K. Hashmi, T.M. Frost and J.W. Bats,Catal. Today, 2001,72, 19–72

    Article  Google Scholar 

  42. A.S.K. Hashmi, T.M. Frost and J.W. Bats,Org. Lett., 2001,3, 3769–3771

    Article  CAS  Google Scholar 

  43. A.S.K. Hashmi, L. Ding, J.W. Bats, P. Fischer and W. Frey,Chem. Eur. J., 2003,9, 4339–4345

    Article  CAS  Google Scholar 

  44. E. Kurpejovic, Universität Stuttgart, recent results during PhD research

  45. R. Salathé, Universität Stuttgart, results from Diploma Thesis and recent results during PhD research

  46. J.W. Dankwardt,Tetrahedron Lett., 2001,42, 5809–5812

    Article  CAS  Google Scholar 

  47. A. Fürstner, V. Mamane,J. Org. Chem., 2002,67, 6264–6267

    Article  Google Scholar 

  48. G. Abbiati, A. Arcadi, G. Bianchi, S. Di Giuseppe, F. Marinelli and E. Rossi,J. Org. Chem., 2003,68, 6959–6966

    Article  CAS  Google Scholar 

  49. N. Asao, K. Takahashi, S. Lee, T. Kasahara and Y. Yamamoto,J. Am. Chem. Soc., 2002,124, 12650–12561

    Article  CAS  Google Scholar 

  50. N. Asao, T. Nogami, S. Lee and Y. Yamamoto,J. Am. Chem. Soc., 2003,125, 10921–10925

    Article  CAS  Google Scholar 

  51. G. Dyker, D. Hildebrandt, J. Liu and K. Merz,Angew. Chem., 2003,115, 4536–4538;Angew. Chem. Int. Ed., 2003,42, 4399–4402

    Article  Google Scholar 

  52. M.T. Reetz and K. Sommer,Eur. J. Org. Chem., 2003, 3485–3496

  53. C. Wei and C.-J. Li,J. Am. Chem. Soc., 2003,125, 9584–9585

    Article  CAS  Google Scholar 

  54. Y. Fukuda, K. Utimoto and H. Nozaki,Heterocycles, 1987,25, 297–300

    Article  CAS  Google Scholar 

  55. Y. Fukuda and K. Utimoto,Synthesis, 1991, 975–978

  56. T.E. Müller,Tetrahedron Lett., 1998,39, 5961–5962

    Article  Google Scholar 

  57. T.E. Müller, M. Grosche, E. Herdtweck, A.-K. Pleier, E. Walter and Y.-K. Yan,Organometallics, 2000,19, 170–183

    Article  Google Scholar 

  58. R. Lok, R.E. Leone and A.J. Williams,J. Org. Chem., 1996,61, 3289–3297

    Article  CAS  Google Scholar 

  59. E. Mizushima, T. Hayashi and M. Tanaka,Org. Lett., 2003,5, 3349–3352

    Article  CAS  Google Scholar 

  60. S. Kobayashi, K. Kakumoto and M. Sugiura,Org. Lett., 2002,4, 1319–1322

    Article  CAS  Google Scholar 

  61. A. Arcadi, S. Di Giuseppe, F. Marinelli and E. Rossi,Adv. Synth. Catal., 2001,343, 443–446

    Article  CAS  Google Scholar 

  62. A. Arcadi, G. Bianchi, S. Di Guiseppe and F. Marinelli,Green Chem., 2003,5, 64–67

    Article  CAS  Google Scholar 

  63. A. Arcadi, S. Di Giuseppe, F. Marinelli and E. Rossi,Tetrahedron Asymm., 2001,12, 2715–2720

    Article  CAS  Google Scholar 

  64. A. Arcadi, M. Chiarini, S. Di Giuseppe and F. Marinelli,Synlett, 2003, 203–206

  65. S. Kamijo and Y. Yamamoto,J. Org. Chem., 2003,68, 4764–4771

    Article  CAS  Google Scholar 

  66. Y. Fukuda and K. Uchimoto, JP 04103552, 1992 [Chem. Abstr., 1992,117, 150554]

  67. Y. Fukuda and K. Utimoto,J. Org. Chem., 1991,56, 3729–3731

    Article  CAS  Google Scholar 

  68. Y. Fukuda and K. Utimoto,Bull. Chem. Soc. Jpn., 1991,64, 2013–2015

    Article  CAS  Google Scholar 

  69. J.H. Teles and M. Schulz (BASF AG), WO-A1 9721648, 1997 [Chem. Abstr., 1997,127, 121499]

    Google Scholar 

  70. J.H. Teles, S. Brode and M. Chabanas,Angew. Chem., 1998,110, 1475–1478;Angew. Chem. Int. Ed., 1998,37, 1415–1418

    Article  Google Scholar 

  71. E. Mizushima, K. Sato, T. Hayashi and M. Tanaka,Angew. Chem., 2002,114, 4745–4747;Angew. Chem. Int. Ed., 2002,41, 4563–4565

    Article  Google Scholar 

  72. L.W. Francisco, D.A. Moreno, J.D. Atwood,Organometallics, 2001,20, 4237–4245

    Article  CAS  Google Scholar 

  73. A. Arcadi, G. Cerichelli, M. Chiarini, S. Di Giuseppe and F. Marinelli,Tetrahedron Lett., 2000,41, 9195–9198

    Article  CAS  Google Scholar 

  74. M. Detlefs, H.G. Raubenheimer and M.W. Esterhuysen,Catal. Today, 2002,72, 29–41

    Article  Google Scholar 

  75. S.K. Schneider, W.A. Herrmann, E. Herdtweck,Z. Anorg. Allg. Chem., 2003,629, 2363–2370

    Article  CAS  Google Scholar 

  76. R. Casado, M. Contel, M. Laguna, P. Romero and S. Sanz,J. Am. Chem. Soc., 2003,123, 11925–11935

    Article  Google Scholar 

  77. M. Méndez, M.P. Munoz, C. Nevade, D.J. Cárdenas, A.M. Echavarren,J. Am. Chem. Soc., 2001,123, 10511–10520

    Article  Google Scholar 

  78. A. Hoffmann-Röder and N. Krause,Org. Lett., 2001,3, 2537–2538

    Article  Google Scholar 

  79. J.A. Marshall and K.G. Pinney,J. Org. Chem., 1993,58, 7180–7184

    Article  CAS  Google Scholar 

  80. N. Krause, A. Hoffmann-Röder and J. Cansius,Synthesis, 2002, 1759–1774

  81. A.S.K. Hashmi and P. Sinha,Adv. Synth. Catal., 2004,346, 432–438

    Article  Google Scholar 

  82. R.T. Baker, P. Nguyen, T.B. Marder and S.A. Westcott,Angew. Chem., 1995,107, 1451–1452;Angew. Chem. Int. Ed. Engl., 1995,34, 1336–1338

    Article  Google Scholar 

  83. R.T. Baker, J.C. Calabrese and S.A. Westcott,J. Organomet. Chem., 1995,498, 109–117

    Article  CAS  Google Scholar 

  84. G. Schmid, H. West, J.-O. Malm, J.-O. Bovin and C. Grenthe,Chem. Eur. J., 1996,2, 1099–1103

    Article  CAS  Google Scholar 

  85. T.N. Mitchell inEncyclopedia of Reagents for Organic Synthesis (Ed. L.A. Paquette), Vol. 4, Wiley, Chichester, 1995, 2664–2666

    Google Scholar 

  86. H. Ito, T. Yajima, J.-i. Tateiwa and A. Hosomi,Tetrahedron Lett., 1999,40, 7807–7810

    Article  CAS  Google Scholar 

  87. H. Ito, T. Yajima, J.-i. Tateiwa and A. Hosomi,J. Chem. Soc., Chem. Commun. 2000, 981–982

  88. A.L. Casado and P. Espinet,Organometallics, 1998,17, 3677–3683

    Article  CAS  Google Scholar 

  89. W.A. Herrmann, J. Kulpe, J. Kellner and H. Riepl, DE 3840600 1990 [Chem. Abstr., 1991,114, 43174]

  90. W.A. Herrmann, J. Kulpe, J. Kellner and H. Riepl, EP 372313 1990 [Chem. Abstr., 1991,114, 143702]

  91. W.A. Herrmann, J. Kulpe, J. Kellner and H. Riepl, US 5,057,6181991

  92. J.T. Gupton,Aldrichim. Acta, 1986,19, 43–46

    CAS  Google Scholar 

  93. J.T. Gupton and S.A. Petrich inEncyclopedia of Reagents for Organic Synthesis (Ed. L.A. Paquette), Vol. 3, Wiley, Chichester, 1995, 2014–2016

    Google Scholar 

  94. R.V. Parish,Gold Bull., 1997,30, 3–12

    Article  CAS  Google Scholar 

  95. R.V. Parish,Gold Bull., 1997,30, 55–62

    Article  CAS  Google Scholar 

  96. R.V. Parish,Gold Bull., 1998,31, 14–21

    Article  CAS  Google Scholar 

  97. J.J. Pesek and W.R. Manson,Inorg. Chem., 1983,22, 2958–2959

    Article  CAS  Google Scholar 

  98. G. Dyker,Angew. Chem., 2000,112, 4407–4409;Angew. Chem., 2000,39, 4237–4239

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

A. Stephen K. Hashmi is professor of organic chemistry at the Universität Stuttgart. He carried out his Diploma and PhD with Professor G. Szeimies at the Ludwig-Maximilians-Universität München in the field of strained organic compounds such as bicyclobutanes and propellanes. His postdoctorate research with Professor B. M. Trost at Stanford University, California, covered transition metal catalysis, specifically then enyne metathesis. His Habilitation with Prof. J. Mulzer at the Freie Universität Berlin, the Johann Wolfgang Goethe-Universität Frankfurt and the Universität Wien, Austria, as well as visits at the University of Tasmania, Australia, and the Universität Marburg focused on both stoichiometric organometallic chemistry and transition metal catalysed organic reactions, which are still the major topics in the group. Recently, activities in the field of bioorganometallic chemistry with enantiomerically pure metallacycloalkanes have been added.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Stephen, A., Hashmi, K. Homogeneous catalysis by gold. Gold Bull 37, 51–65 (2004). https://doi.org/10.1007/BF03215517

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03215517

Keywords

Navigation