Organometallic Homogeneous Catalysis - Quo vadis?

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 10, 1997, Pages 1048-1067

  Herrmann, Wolfgang A ^a   Cornils, Boy ^b  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b SANOFI   (France)

Author keywords

Homogeneous catalysis; Industrial chemistry; Organometallic chemistry; Polymers; Reagents

Indexed keywords

EID: 0030796074     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199710481     Document Type: Review

References (339)

1. x catalysis) is even older but does not involve metals or metal complexes as catalysts.
2. The word serendipity was coined by Horace Walpole in a letter to Sir Horace Mann in 1754 and is based on the fairy tale about the adventures of "The Three Princes of Serendip" (or Serendib, an ancient name for Ceylon, now known as Sri Lanka): R. M. Roberts, Serendipity - Accidental Discoveries in Science, Wiley, New York 1989. This term is now being used for fortunate, totally unexpected discoveries - discoveries by accident and sagacity.
3. 3 with ethylene.
4. The first comprehensive monograph, Die Chemie der Metallorganischen Verbindungen by E. Krause and A. von Grosse [5a], comes to mind. It appeared in 1937 just before hydroformylation was discovered. In the 900-page book only little is reported on the present-day champions of homogeneous catalysis (for example three pages and six references for Pt), and there is no mention at all of Co, Rh, or Pd. What a contrast when the monumental work Comprehensive Organometallic Chemistry (nine volumes, 8750 printed pages) appeared 45 years later; the second edition comprising 14 volumes is already in print! A total of about 24000 organometallic compounds has been registered by the Chemical Abstract Service up to now. The Journal of Organometallic Chemistry was chartered in 1963 and, in the meantime, has seen 500 volumes with a total of 20000 papers on 194000 journal pages! Two more key journals, the Journal of Molecular Catalysis (1975) and Organometallics (1982), broadly cover catalytic applications of organometallic compounds. Early monographs and reviews have recognized this inter-dependence.
5. The first comprehensive monograph, Die Chemie der Metallorganischen Verbindungen by E. Krause and A. von Grosse [5a], comes to mind. It appeared in 1937 just before hydroformylation was discovered. In the 900-page book only little is reported on the present-day champions of homogeneous catalysis (for example three pages and six references for Pt), and there is no mention at all of Co, Rh, or Pd. What a contrast when the monumental work Comprehensive Organometallic Chemistry (nine volumes, 8750 printed pages) appeared 45 years later; the second edition comprising 14 volumes is already in print! A total of about 24000 organometallic compounds has been registered by the Chemical Abstract Service up to now. The Journal of Organometallic Chemistry was chartered in 1963 and, in the meantime, has seen 500 volumes with a total of 20000 papers on 194000 journal pages! Two more key journals, the Journal of Molecular Catalysis (1975) and Organometallics (1982), broadly cover catalytic applications of organometallic compounds. Early monographs and reviews have recognized this inter-dependence.
6. The first comprehensive monograph, Die Chemie der Metallorganischen Verbindungen by E. Krause and A. von Grosse [5a], comes to mind. It appeared in 1937 just before hydroformylation was discovered. In the 900-page book only little is reported on the present-day champions of homogeneous catalysis (for example three pages and six references for Pt), and there is no mention at all of Co, Rh, or Pd. What a contrast when the monumental work Comprehensive Organometallic Chemistry (nine volumes, 8750 printed pages) appeared 45 years later; the second edition comprising 14 volumes is already in print! A total of about 24000 organometallic compounds has been registered by the Chemical Abstract Service up to now. The Journal of Organometallic Chemistry was chartered in 1963 and, in the meantime, has seen 500 volumes with a total of 20000 papers on 194000 journal pages! Two more key journals, the Journal of Molecular Catalysis (1975) and Organometallics (1982), broadly cover catalytic applications of organometallic compounds. Early monographs and reviews have recognized this inter-dependence.
7. The first comprehensive monograph, Die Chemie der Metallorganischen Verbindungen by E. Krause and A. von Grosse [5a], comes to mind. It appeared in 1937 just before hydroformylation was discovered. In the 900-page book only little is reported on the present-day champions of homogeneous catalysis (for example three pages and six references for Pt), and there is no mention at all of Co, Rh, or Pd. What a contrast when the monumental work Comprehensive Organometallic Chemistry (nine volumes, 8750 printed pages) appeared 45 years later; the second edition comprising 14 volumes is already in print! A total of about 24000 organometallic compounds has been registered by the Chemical Abstract Service up to now. The Journal of Organometallic Chemistry was chartered in 1963 and, in the meantime, has seen 500 volumes with a total of 20000 papers on 194000 journal pages! Two more key journals, the Journal of Molecular Catalysis (1975) and Organometallics (1982), broadly cover catalytic applications of organometallic compounds. Early monographs and reviews have recognized this inter-dependence.
8. The first comprehensive monograph, Die Chemie der Metallorganischen Verbindungen by E. Krause and A. von Grosse [5a], comes to mind. It appeared in 1937 just before hydroformylation was discovered. In the 900-page book only little is reported on the present-day champions of homogeneous catalysis (for example three pages and six references for Pt), and there is no mention at all of Co, Rh, or Pd. What a contrast when the monumental work Comprehensive Organometallic Chemistry (nine volumes, 8750 printed pages) appeared 45 years later; the second edition comprising 14 volumes is already in print! A total of about 24000 organometallic compounds has been registered by the Chemical Abstract Service up to now. The Journal of Organometallic Chemistry was chartered in 1963 and, in the meantime, has seen 500 volumes with a total of 20000 papers on 194000 journal pages! Two more key journals, the Journal of Molecular Catalysis (1975) and Organometallics (1982), broadly cover catalytic applications of organometallic compounds. Early monographs and reviews have recognized this inter-dependence.
9. See a) E. Krause, A. von Grosse, Die Chemie der Metallorganischen Verbindungen, Gebrüder Borntraeger, Berlin, 1937; reprint: Dr. Martin Sändig, Wiesbaden, 1965. Specific treatments of organomagnesium (Grignard) and organoalkaline metal compounds are older, see for example W. Runge, Organometallverbindungen, Wissenschaftliche Verlagsgesellschaft, Stuttgart, 1931 (2nd ed. 1944); b) G. Wilkinson in Comprehensive Organometallic Chemistry (Eds. : F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982 (2nd edition 1996); c) Dictionary of Organometallic Compounds (Ed.: J. Buckingham), Chapman and Hall, London, 1984; d) Dictionary of Organometallic Compounds (Eds.: B. J. Aylett M. F. Lappert, P. L. Pauson), 2nd ed., Chapman and Hall, London, 1995.
10. See a) E. Krause, A. von Grosse, Die Chemie der Metallorganischen Verbindungen, Gebrüder Borntraeger, Berlin, 1937; reprint: Dr. Martin Sändig, Wiesbaden, 1965. Specific treatments of organomagnesium (Grignard) and organoalkaline metal compounds are older, see for example W. Runge, Organometallverbindungen, Wissenschaftliche Verlagsgesellschaft, Stuttgart, 1931 (2nd ed. 1944); b) G. Wilkinson in Comprehensive Organometallic Chemistry (Eds. : F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982 (2nd edition 1996); c) Dictionary of Organometallic Compounds (Ed.: J. Buckingham), Chapman and Hall, London, 1984; d) Dictionary of Organometallic Compounds (Eds.: B. J. Aylett M. F. Lappert, P. L. Pauson), 2nd ed., Chapman and Hall, London, 1995.
11. See a) E. Krause, A. von Grosse, Die Chemie der Metallorganischen Verbindungen, Gebrüder Borntraeger, Berlin, 1937; reprint: Dr. Martin Sändig, Wiesbaden, 1965. Specific treatments of organomagnesium (Grignard) and organoalkaline metal compounds are older, see for example W. Runge, Organometallverbindungen, Wissenschaftliche Verlagsgesellschaft, Stuttgart, 1931 (2nd ed. 1944); b) G. Wilkinson in Comprehensive Organometallic Chemistry (Eds. : F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982 (2nd edition 1996); c) Dictionary of Organometallic Compounds (Ed.: J. Buckingham), Chapman and Hall, London, 1984; d) Dictionary of Organometallic Compounds (Eds.: B. J. Aylett M. F. Lappert, P. L. Pauson), 2nd ed., Chapman and Hall, London, 1995.
12. See a) E. Krause, A. von Grosse, Die Chemie der Metallorganischen Verbindungen, Gebrüder Borntraeger, Berlin, 1937; reprint: Dr. Martin Sändig, Wiesbaden, 1965. Specific treatments of organomagnesium (Grignard) and organoalkaline metal compounds are older, see for example W. Runge, Organometallverbindungen, Wissenschaftliche Verlagsgesellschaft, Stuttgart, 1931 (2nd ed. 1944); b) G. Wilkinson in Comprehensive Organometallic Chemistry (Eds. : F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982 (2nd edition 1996); c) Dictionary of Organometallic Compounds (Ed.: J. Buckingham), Chapman and Hall, London, 1984; d) Dictionary of Organometallic Compounds (Eds.: B. J. Aylett M. F. Lappert, P. L. Pauson), 2nd ed., Chapman and Hall, London, 1995.
13. See a) E. Krause, A. von Grosse, Die Chemie der Metallorganischen Verbindungen, Gebrüder Borntraeger, Berlin, 1937; reprint: Dr. Martin Sändig, Wiesbaden, 1965. Specific treatments of organomagnesium (Grignard) and organoalkaline metal compounds are older, see for example W. Runge, Organometallverbindungen, Wissenschaftliche Verlagsgesellschaft, Stuttgart, 1931 (2nd ed. 1944); b) G. Wilkinson in Comprehensive Organometallic Chemistry (Eds. : F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982 (2nd edition 1996); c) Dictionary of Organometallic Compounds (Ed.: J. Buckingham), Chapman and Hall, London, 1984; d) Dictionary of Organometallic Compounds (Eds.: B. J. Aylett M. F. Lappert, P. L. Pauson), 2nd ed., Chapman and Hall, London, 1995.
14. a) "The 16-and 18-Electron Rule in Organometallic Chemistry and Homogeneous Catalysis": C. A. Tolman, Chem. Soc. Rev. 1972, 1, 337;
15. b) Fundamental Research in Homogeneous Catalysis (Eds.: M. Tsutsui, R. Ugo), Plenum, New York, 1977;
16. c) J. K. Kochi, Organometallic Mechanisms and Catalysis, Academic Press, New York, 1978;
17. d) J. Halpern, Pure Appl. Chem. 1983, 55, 99.
18. G. W. Parshall, R. E. Putscher, J. Chem. Educ. 1986, 63, 189.
19. a) R. Schlögl, Angew. Chem. 1993, 102, 402; Angew. Chem. Int. Ed. Engl. 1993, 32, 381;
20. a) R. Schlögl, Angew. Chem. 1993, 102, 402; Angew. Chem. Int. Ed. Engl. 1993, 32, 381;
21. b) ibid. 1994, 106, 319 and 1994, 33, 311
22. b) ibid. 1994, 106, 319 and 1994, 33, 311
23. J. M. Thomas, K. I. Zamaraev, Angew. Chem. 1994, 106, 316; Angew. Chem. Int. Ed. Engl. 1994, 33, 308.
24. J. M. Thomas, K. I. Zamaraev, Angew. Chem. 1994, 106, 316; Angew. Chem. Int. Ed. Engl. 1994, 33, 308.
25. Review: W. A. Herrmann, Angew. Chem. 1982, 94, 118; Angew. Chem. Int. Ed. Engl. 1982, 21, 117.
26. Review: W. A. Herrmann, Angew. Chem. 1982, 94, 118; Angew. Chem. Int. Ed. Engl. 1982, 21, 117.
27. See for example a) B. C. Gates, Catalytic Chemistry, Wiley, New York, 1992; b) C. Lecuyer, F. Quignard, A. Choplin, D. Olivier, J.-M. Basset, Angew. Chem. 1991, 103, 1692; Angew. Chem. Int. Ed. Engl. 1991, 36, 1660; c) T. A. Budzichowski, S. T. Chacon, M. Chrisholm, F. J. Feher, W. Streib, J. Am. Chem. Soc. 1991, 113, 689; d) W. A. Herrmann, R. Anwander, V. Dufaud, W. Scherer, Angew. Chem. 1994, 106, 133; Angew. Chem. Int. Ed. Engl. 1994, 33, 1285.
28. See for example a) B. C. Gates, Catalytic Chemistry, Wiley, New York, 1992; b) C. Lecuyer, F. Quignard, A. Choplin, D. Olivier, J.-M. Basset, Angew. Chem. 1991, 103, 1692; Angew. Chem. Int. Ed. Engl. 1991, 36, 1660; c) T. A. Budzichowski, S. T. Chacon, M. Chrisholm, F. J. Feher, W. Streib, J. Am. Chem. Soc. 1991, 113, 689; d) W. A. Herrmann, R. Anwander, V. Dufaud, W. Scherer, Angew. Chem. 1994, 106, 133; Angew. Chem. Int. Ed. Engl. 1994, 33, 1285.
29. See for example a) B. C. Gates, Catalytic Chemistry, Wiley, New York, 1992; b) C. Lecuyer, F. Quignard, A. Choplin, D. Olivier, J.-M. Basset, Angew. Chem. 1991, 103, 1692; Angew. Chem. Int. Ed. Engl. 1991, 36, 1660; c) T. A. Budzichowski, S. T. Chacon, M. Chrisholm, F. J. Feher, W. Streib, J. Am. Chem. Soc. 1991, 113, 689; d) W. A. Herrmann, R. Anwander, V. Dufaud, W. Scherer, Angew. Chem. 1994, 106, 133; Angew. Chem. Int. Ed. Engl. 1994, 33, 1285.
30. See for example a) B. C. Gates, Catalytic Chemistry, Wiley, New York, 1992; b) C. Lecuyer, F. Quignard, A. Choplin, D. Olivier, J.-M. Basset, Angew. Chem. 1991, 103, 1692; Angew. Chem. Int. Ed. Engl. 1991, 36, 1660; c) T. A. Budzichowski, S. T. Chacon, M. Chrisholm, F. J. Feher, W. Streib, J. Am. Chem. Soc. 1991, 113, 689; d) W. A. Herrmann, R. Anwander, V. Dufaud, W. Scherer, Angew. Chem. 1994, 106, 133; Angew. Chem. Int. Ed. Engl. 1994, 33, 1285.
31. See for example a) B. C. Gates, Catalytic Chemistry, Wiley, New York, 1992; b) C. Lecuyer, F. Quignard, A. Choplin, D. Olivier, J.-M. Basset, Angew. Chem. 1991, 103, 1692; Angew. Chem. Int. Ed. Engl. 1991, 36, 1660; c) T. A. Budzichowski, S. T. Chacon, M. Chrisholm, F. J. Feher, W. Streib, J. Am. Chem. Soc. 1991, 113, 689; d) W. A. Herrmann, R. Anwander, V. Dufaud, W. Scherer, Angew. Chem. 1994, 106, 133; Angew. Chem. Int. Ed. Engl. 1994, 33, 1285.
32. See for example a) B. C. Gates, Catalytic Chemistry, Wiley, New York, 1992; b) C. Lecuyer, F. Quignard, A. Choplin, D. Olivier, J.-M. Basset, Angew. Chem. 1991, 103, 1692; Angew. Chem. Int. Ed. Engl. 1991, 36, 1660; c) T. A. Budzichowski, S. T. Chacon, M. Chrisholm, F. J. Feher, W. Streib, J. Am. Chem. Soc. 1991, 113, 689; d) W. A. Herrmann, R. Anwander, V. Dufaud, W. Scherer, Angew. Chem. 1994, 106, 133; Angew. Chem. Int. Ed. Engl. 1994, 33, 1285.
33. H. Heinemann, CHEMTECH 1971, 286.
34. a) H. Pommer, Angew. Chem. 1960, 72, 811;
35. b) Angew. Chem. 1977, 89, 437; Angew. Chem. Int. Ed. Engl. 1977, 16, 423;
36. b) Angew. Chem. 1977, 89, 437; Angew. Chem. Int. Ed. Engl. 1977, 16, 423;
37. c) W. Reif, H. Grassner, Chem. Ing. Tech. 1973, 45, 646;
38. d) H. Pommer, P. C. Thieme, Top. Curr. Chem. 198, 109, 165;
39. e) J. Paust, Pure Appl. Chem. 1991, 63, 45;
40. f) W. Sarnecki, H. Pommer (BASFAG), DE-A 1060368, 1957;
41. g) H. Pommer, W. Sarnecki (BASFAG), DE-A 1068702, 1958 [Chem. Abstr. 1961, 55, 10812e];
42. h) W. Himmele, F. J. Müller. W. Aquila (BASFAG), DE-A 2039078, 1972.
43. P. Fitton, H. Moffet (Hoffmann-La Roche), US-A 4124619, 1978 [Chem. Abstr. 1979, 86, 105966y].
44. a) Anonymus, Chem. Ind. (Duesseldorf) 1996, 13, 483;
45. b) mechanistic aspects: P. M. Maitlis, A. Haynes, G. J. Sunley, M. J. Howard, J. Chem. Soc. Dalton Trans. 1996, 2187.
46. J. D. Atwood, Mechanisms of Inorganic and Organometallic Reactions, Brooks/Cole, Monterey, Canada, 1985.
47. a) J. F. Waller, J. Mol. Catal. 1985, 31, 123;
48. b) G. W. Parshall, Organometallics 1987, 6, 687;
49. c) E. Drent, Pure Appl. Chem. 1990, 62, 661.
50. a) W. A. Herrmann, C. Broßmer, K. Öfele. C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989; Angew. Chem. Int. Ed. Engl. 1995, 35, 1844;
51. a) W. A. Herrmann, C. Broßmer, K. Öfele. C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989; Angew. Chem. Int. Ed. Engl. 1995, 35, 1844;
52. b) M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Broßmer, ibid. 1995, 107, 1992 and 1995, 35, 1846;
53. b) M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Broßmer, ibid. 1995, 107, 1992 and 1995, 35, 1846;
54. c) J. J. Masters, J. T. Link, L. B. Snyder, W. B. Young, S. J. Danishefsky, ibid. 1995, 107, 1886 and 1995, 35, 1723;
55. c) J. J. Masters, J. T. Link, L. B. Snyder, W. B. Young, S. J. Danishefsky, ibid. 1995, 107, 1886 and 1995, 35, 1723;
56. d) review: K. C. Nicolaou, R. K. Guy, ibid. 1995, 107, 2247 and 1995, 35, 2079.
57. d) review: K. C. Nicolaou, R. K. Guy, ibid. 1995, 107, 2247 and 1995, 35, 2079.
58. J. Louie, J. F. Hartwig, Angew. Chem. 1996, 108, 2531; Angew. Chem. Int. Ed. Engl. 1996, 36, 2359.
59. J. Louie, J. F. Hartwig, Angew. Chem. 1996, 108, 2531; Angew. Chem. Int. Ed. Engl. 1996, 36, 2359.
60. a) W. A. Herrmann, J. Organomet. Chem. 1995, 500, 149;
61. b) W. A. Herrmann, F.-E. Kühn, Acc. Chem. Res. 1997, in press.
62. See for example a) T. Ziegler, Chem. Rev. 1991, 91, 651; b) Density Functional Methods in Chemistry (Eds.: J. K. Labanowski, J. W. Andzelm), Springer, New York, 1991; c) O. D. Häberlein, N. Rösch, J. Phys. Chem. 1993, 4970; d) S. Köstlmeier, O. D. Häberlein, N. Rösch, W. A. Herrmann, B. Solouki, H. Bock, Organometallics 1996, 15, 1872.
63. See for example a) T. Ziegler, Chem. Rev. 1991, 91, 651; b) Density Functional Methods in Chemistry (Eds.: J. K. Labanowski, J. W. Andzelm), Springer, New York, 1991; c) O. D. Häberlein, N. Rösch, J. Phys. Chem. 1993, 4970; d) S. Köstlmeier, O. D. Häberlein, N. Rösch, W. A. Herrmann, B. Solouki, H. Bock, Organometallics 1996, 15, 1872.
64. See for example a) T. Ziegler, Chem. Rev. 1991, 91, 651; b) Density Functional Methods in Chemistry (Eds.: J. K. Labanowski, J. W. Andzelm), Springer, New York, 1991; c) O. D. Häberlein, N. Rösch, J. Phys. Chem. 1993, 4970; d) S. Köstlmeier, O. D. Häberlein, N. Rösch, W. A. Herrmann, B. Solouki, H. Bock, Organometallics 1996, 15, 1872.
65. See for example a) T. Ziegler, Chem. Rev. 1991, 91, 651; b) Density Functional Methods in Chemistry (Eds.: J. K. Labanowski, J. W. Andzelm), Springer, New York, 1991; c) O. D. Häberlein, N. Rösch, J. Phys. Chem. 1993, 4970; d) S. Köstlmeier, O. D. Häberlein, N. Rösch, W. A. Herrmann, B. Solouki, H. Bock, Organometallics 1996, 15, 1872.
66. P. Comba, T. W. Hambley, Molecular Modelling, VCH, Weinheim, 1995.
67. J. S. Giovannetti, C. M. Kelly, C. R. Landis, J. Am. Chem. Soc. 1993, 115, 4040.
68. a) M. W. Balakos, S. S. C. Chuang, J. Catal. 1995, 151, 253, 266;
69. b) R. M. Deshpande, R. V. Chaudhari, Ind. Eng. Chem. Res. 1988, 27, 1996;
70. c) S. S. Divekar, R. M. Deshpande, R. V. Chaudhari, Catal. Lett. 1993, 21, 191.
71. R. V. Gholap, O. M. Kut, J. R. Bourne, Ind. Eng. Chem. Res. 1992, 31, 1597, 2446.
72. a) Applied Homogeneous Catalysis with Organometallic Compounds (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996;
73. b) J. Bargon in ref. [26a], chap. 3.1.3, p. 672.
74. M. J. Baker, J. R. Dilworth, J. G. Glenn, N. Wheatley (BP Chemicals Ltd.), EP-A 0632006, 1994 [Chem. Abstr. 1995, 122, 164060h].
75. F. R. Hartley, Supported Metal Complexes. A New Generation of Catalysts, Reidel, Dordrecht, 1985.
76. a) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. 1995, 107, 2602; Angew. Chem. Int. Ed. Engl. 1995, 34, 3005;
77. a) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. 1995, 107, 2602; Angew. Chem. Int. Ed. Engl. 1995, 34, 3005;
78. b) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher (Hoechst AG), DE-A 4447066, 4447067, 4447068, 1994 [Chem. Abstr. 1996, 125, 143019y];
79. c) W. A. Herrmann, C. Köcher. L. J. Gooßen. G. R. J. Artus, Chem. Eur. J. 1996, 2, 1627;
80. d) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, ibid. 1996, 2, 772;
81. e) W. A. Herrmann, C. Köcher, L. J. Gooßen, G. R. J. Artus, ibid. 1996, 2, 229;
82. f) review: W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, in press; Angew. Chem. Int. Ed. Engl. 1997, 36, in press;
83. f) review: W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, in press; Angew. Chem. Int. Ed. Engl. 1997, 36, in press;
84. g) W. A. Herrmann, L. J. Gooßen, C. Köcher, G. R. J. Artus, ibid. 1996, 108, 2980 and 1996, 35, 2805.
85. g) W. A. Herrmann, L. J. Gooßen, C. Köcher, G. R. J. Artus, ibid. 1996, 108, 2980 and 1996, 35, 2805.
86. a) B. Pugin, F. Spindler, M. Müller (Ciba-Geigy AG), EP-A 496699-A1, EP-A 496700, 1991 [Chem. Abstr. 1992, 117, 212722w, 234253w];
87. b) B. Pugin, H. Landert, L. Martin, Abstr. Pap. Xth Int. Conf. Homogen. Catal., 1996, Princeton, p. CL-5.
88. U. Romano, A. Esposito, F. Maspero, C. Neri, M. G. Clerici, Chim. Ind. (Milano 1990, 72, 610.
89. Review: S. L. Scott, J.-M. Basset, G. P. Niccolai, C. C. Santini, J.-P. Candy, C. Lecuyer, F. Quignard, A. Choplin, New J. Chem. 1994, 18, 115.
90. V. Dufaud, J.-M. Basset, Science, 1997, in press.
91. C. C. Freyhardt, M. Tsapatsis, R. F. Lobo, K. J. Balkus, Jr., M. E. Davis, Nature 1996, 381, 295.
92. P. Behrens, Angew. Chem. 1996, 108, 561; Angew. Chem. Int. Ed. Engl. 1996, 35, 515.
93. P. Behrens, Angew. Chem. 1996, 108, 561; Angew. Chem. Int. Ed. Engl. 1996, 35, 515.
94. D. M. Antonelli, J. Y. Ying, Angew. Chem. 1996, 108, 461; Angew. Chem. Int. Ed. Engl. 1996, 35, 426.
95. D. M. Antonelli, J. Y. Ying, Angew. Chem. 1996, 108, 461; Angew. Chem. Int. Ed. Engl. 1996, 35, 426.
96. J.-A. M. Andersen, A. W. C. Currie, Chem. Commun. 1996, 1543.
97. a) D. Avnir, J. Blum, A. Rosenfeld, H. Schumann, H. Sertchook, S. Wernik, Abstr. Pap. 9th Int. Symp. Homogen. Catal, Jerusalem (Israel), 1994, p. 144;
98. b) G. Wulff, Angew. Chem. 1995, 107, 1958; Angew. Chem. Int. Ed. Engl. 1995, 34, 1812.
99. b) G. Wulff, Angew. Chem. 1995, 107, 1958; Angew. Chem. Int. Ed. Engl. 1995, 34, 1812.
100. Coordination Chemistry of Mucfocyclic Compounds (Ed.: G. A. Melson), Plenum, New York, 1979.
101. a) M. de Sousa Healy, A. J. Rest. Adv. Innrg. Radiachem. 1978, 21, 1;
102. b) J. Steinke, D. C. Sherringlon, I. R. Dunkin, Adv. Polym. Sci. 1995, 123, 81.
103. P.O. Schultz, Angew. Chem. 1989, 101, 1336; Angew. Chem. Int. Ed. Engl. 1989, 28, 1283.
104. P.O. Schultz, Angew. Chem. 1989, 101, 1336; Angew. Chem. Int. Ed. Engl. 1989, 28, 1283.
105. a) H. Hönig, R. Rogi-Kohlenprath, H. Weber in Chiral Reactions in Heterogeneous Catalysis (Eds. : G. Jannes, V. Dubois), Plenum, Oxford, 1995, p. 135;
106. b) C. Exl, I. Francesconi, H. Hönig, R. Rogi-Kohlenprath, vorgetragen auf dem 8th Int. Symp. Relat. Homogen. Heterogen. Catal. Balatonfüred (Hungary), 1995.
107. a) J. M. Lehn, Angew. Chem. 1988,100, 91; Angew. Chem. Int. Ed. Engl. 1988, 27, 89;
108. a) J. M. Lehn, Angew. Chem. 1988,100, 91; Angew. Chem. Int. Ed. Engl. 1988, 27, 89;
109. b) D. J. Cram, ibid. 1988, 100, 1041 and 1988, 27, 1009.
110. b) D. J. Cram, ibid. 1988, 100, 1041 and 1988, 27, 1009.
111. A. Müller, H. Reuter, S. Dillinger, Angew. Chem. 1995, 107, 2505; Angew. Chem. Int. Ed. Engl. 1995, 35, 2328.
112. A. Müller, H. Reuter, S. Dillinger, Angew. Chem. 1995, 107, 2505; Angew. Chem. Int. Ed. Engl. 1995, 35, 2328.
113. D. E. De Vos, F. Thibault-Starcyc, P. P. Knops-Gerrits, R. F. Parton, P. A. Jacobs, Macromol. Symp. 1994, 80, 157.
114. a) Handbook of Heterogeneous Catalysis (Eds.: G. Ertl, H. Knözinger, J. Weitkamp), Wiley-VCH, Weinheim, 1997;
115. b) J. M. Thomas, J. W. Thomas, Principles and Practice of Heterogeneous Catalysis, VCH, Weinheim, 1996.
116. a) Monograph: Aqueous-Phase Organometallic Catalysis (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 1998, in press;
117. b) Review: W. A. Herrmann, C.W. Kohlpaintner, Angew. Chem. 1993, 105, 1588, Angew. Chem. Int. Ed. Engl. 1993, 32, 1524.
118. b) Review: W. A. Herrmann, C.W. Kohlpaintner, Angew. Chem. 1993, 105, 1588, Angew. Chem. Int. Ed. Engl. 1993, 32, 1524.
119. a) I. T. Horváth, J. Rábai, Science 1994, 266, 72;
120. b) M. Vogt, Ph.D. thesis. Rheinisch-Westfälische Technische Hochschule Aachen (Germany), 1991;
121. c) I. T. Horváth, J. Rábai (Exxon Research and Engineering Co.), EP-A 0633062, 1995 [Chem. Abstr. 1995, 123, 87349a], US-A 5463082, 1995;
122. d) I. T. Horváth in ref. [26a], chap. 3.1.1.2, p. 601;
123. e) D. P. Curran, S. Hadida, J. Am. Chem. Soc. 1996, 118, 2532.
124. Monograph: Clusters and Colloids (Ed.: G. Schmid), VCH, Weinheim, 1994.
125. M. T. Reetz, S. A. Quaiser, Angew. Chem. 1995, 107, 2461; Angew. Chem. Int. Ed. Engl. 1995, 34, 2240.
126. M. T. Reetz, S. A. Quaiser, Angew. Chem. 1995, 107, 2461; Angew. Chem. Int. Ed. Engl. 1995, 34, 2240.
127. H. Vahrenkamp, Adv. Organomet. Chem. 1983, 22, 169.
128. a) H. Bönnemann, W. Brijoux, R. Brinkmann, E. Dinjus, T. Jouen, B. Korall, Angew. Chem. 1991, 103, 1344; Angew. Chem. Int. Ed. Engl. 1991, 30, 1312;
129. a) H. Bönnemann, W. Brijoux, R. Brinkmann, E. Dinjus, T. Jouen, B. Korall, Angew. Chem. 1991, 103, 1344; Angew. Chem. Int. Ed. Engl. 1991, 30, 1312;
130. b) H. Bönnemann, W. Brijoux, R. Brinkmann, R. Fretzen, T. Joussen, R. Köppler, B. Korall, P. Neiteler, J. Richter, J. Mol. Catal. 1994, 86, 129;
131. c) L. N. Lewis, J. Stein, K. A. Smith in Progress in Organosilicon Chemistry (Eds.: B. Marciniec, J. Chojonovski), Gordon-Beach, Langhorne (USA), 1995, p. 263;
132. d) T. J. Wehrli, A. Baiker, D. M. Monti, H. U. Blaser, J. Mol. Cat. 1990, 61, 207;
133. e) Workshop on Bimetallic Effects in Chemistry, European Science Foundation, Parma (Italy), 1995.
134. a) Ref. [46a];
135. b) J. H. Sinfelt, Bimetallic Catalysts - Discoveries, Concepts and Applications, Wiley, New York, 1983.
136. J. R. Anderson, M. Boudart, Catalysis - Science and Technology, Springer, Berlin, 1981.
137. a) M. E. Broussard, B. Juma, S. G. Train, W.-J. Peng, S. A. Laneman, G. G. Stanley, Science 1993, 260, 1784;
138. b) G. Süss-Fink, Angew. Chem. 1994, 106, 71; Angew. Chem. Int. Ed. Engl. 1994, 33, 67;
139. b) G. Süss-Fink, Angew. Chem. 1994, 106, 71; Angew. Chem. Int. Ed. Engl. 1994, 33, 67;
140. c) R. C. Matthews, D. K. Howell, W-J. Peng, S. G. Train, W. D. Treleaven, G. G. Stanley, ibid. 1996, 108, 2402 and 1996, 35, 2253;
141. c) R. C. Matthews, D. K. Howell, W-J. Peng, S. G. Train, W. D. Treleaven, G. G. Stanley, ibid. 1996, 108, 2402 and 1996, 35, 2253;
142. d) W.-J. Peng, S. G. Train, D. K. Howell, F. R. Fronczek, G. G. Stanley, Chem. Commun. 1996, 2607.
143. B. Cornils, W. Konkol, H. W. Bach, G. Dämbkes, W. Gick, E. Wiebus, H. Bahrmann (Ruhrchemie AG). DE-A 3415968, 1984[Chem. Abstr. 1986, 104, 209147p], EP-A 0160249, 1985 [Chem. Abstr.].
144. J. W. Rathke, R. J. Klinger (Argonne Natl. Lab.), US-A 5198589, 1993 [Chem. Abstr. 1993, 119, 141-597 n].
145. R. G. Jessop, T. Ikariya, R. Noyori, Nature (London) 1994, 368, 231; ibid. 1995, 269, 1065; Chem. Rev. 1995, 95, 259; see also W. Leitner, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2391.
146. R. G. Jessop, T. Ikariya, R. Noyori, Nature (London) 1994, 368, 231; ibid. 1995, 269, 1065; Chem. Rev. 1995, 95, 259; see also W. Leitner, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2391.
147. R. G. Jessop, T. Ikariya, R. Noyori, Nature (London) 1994, 368, 231; ibid. 1995, 269, 1065; Chem. Rev. 1995, 95, 259; see also W. Leitner, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2391.
148. R. G. Jessop, T. Ikariya, R. Noyori, Nature (London) 1994, 368, 231; ibid. 1995, 269, 1065; Chem. Rev. 1995, 95, 259; see also W. Leitner, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2391.
149. R. G. Jessop, T. Ikariya, R. Noyori, Nature (London) 1994, 368, 231; ibid. 1995, 269, 1065; Chem. Rev. 1995, 95, 259; see also W. Leitner, Angew. Chem. 1995, 107, 2207; Angew. Chem. Int. Ed. Engl. 1995, 34, 2391.
150. Top. Curr. Chem. (Ed.: W. A. Herrmann), 1996, 179.
151. a) S. L. Stinson, Chem. Eng. News 1994, 72(38), 33;
152. b) ibid. 1995, 73(41), 44.
153. C. Botteghi, S. Paganelli, A. Schionato, M. Marchetti, Chirality 1991, 3, 355.
154. a) L. S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, CA, 1994;
155. b) D. Seebach, Angew. Chem. 1990, 102, 1363; Angew. Chem. Int. Ed. Engl. 1990, 29, 1320.
156. b) D. Seebach, Angew. Chem. 1990, 102, 1363; Angew. Chem. Int. Ed. Engl. 1990, 29, 1320.
157. H. Brunner, W. Zettlmeier, Handbook of Enantioselective Catalysis, VCH, Weinheim, 1993.
158. a) Y. Orito, S. Imai, S. Niwa, J. Chem. Soc. Jpn. 1979, 1118;
159. b) H.-U. Blaser, H. P. Jalett in Heterogen. Catal. Fine Chem. III (Ed.: M. Guisnet), Elsevier, Amsterdam, 1993, p. 139;
160. B. Minder, T. Mallat, A. Baiker, G. Wang, T. Heinz, A. Pfaltz, J. Catal. 1995, 154, 371;
161. K. E. Simons, G. Wang, T. Heinz, T. Giger, T. Mallat, A. Pfaltz, A. Baiker, Tetrahedron: Asymmetry 1995, 6, 505.
162. a) R. Noyori, Science 1990, 248, 1194; Chem. Soc. Rev. 1989, 18, 187;
163. a) R. Noyori, Science 1990, 248, 1194; Chem. Soc. Rev. 1989, 18, 187;
164. b) W. A. Herrmann, R. Eckl. unpublished results;
165. c) N. Sakai, S. Mano, K. Nozaki, H. Takaya, ibid. 1993, 115, 7033;
166. d) N. Sakai, K. Nozaki, H. Takaya, J. Chem. Soc. Chem. Commun. 1994, 395;
167. e) T. Higashizima, N. Sakai, S. Mano, K. Nozaki, H. Takaya, Tetrahedron Lett. 1994, 35, 2023; K. Nozaki, T. Nanno, H. Takaya, J. Organomet. Chem. 1997, 527, 103.
168. e) T. Higashizima, N. Sakai, S. Mano, K. Nozaki, H. Takaya, Tetrahedron Lett. 1994, 35, 2023; K. Nozaki, T. Nanno, H. Takaya, J. Organomet. Chem. 1997, 527, 103.
169. A. Togni, L. M. Venanzi, Angew. Chem. 1994, 106, 517; Angew. Chem. Int. Ed. Engl. 1994, 34, 497.
170. A. Togni, L. M. Venanzi, Angew. Chem. 1994, 106, 517; Angew. Chem. Int. Ed. Engl. 1994, 34, 497.
171. a) A. Pfaltz, Mod. Synth. Methods 1989, 5, 199;
172. b) T. Aratani, Pure Appl. Chem. 1985, 57, 1839.
173. a) E. N. Jacobsen, L. Deng, Y. Furukawa, E. Martinez, Pure Appl. Chem. 1994, 50, 4323;
174. b) E. N. Jacobsen in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, p. 159-202;
175. c) B. D. Brandes, E. N. Jacobsen, Tetrahedron Lett. 1995, 36, 5123;
176. d) J. Org. Chem. 1994, 59, 4378.
177. a) M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1986, 108. 6071;
178. b) M. Kitamura, S. Okada, S. Suga, R. Noyori, ibid. 1989, 111, 4028;
179. c) K. Soai, T. Shibata, H. Morioka, K. Choji, Nature 1993, 378, 767.
180. Reviews: a) A. D. Ryabov, Angew. Chem. 1991, 103, 945; Angew. Chem. Int. Ed. Engl. 1991, 30, 931; b) N. Sträter, W. N. Lipscomb, T. Klabunde, B. Krebs, ibid. 1996, 108, 2158 and 1996, 35, 2024.
181. Reviews: a) A. D. Ryabov, Angew. Chem. 1991, 103, 945; Angew. Chem. Int. Ed. Engl. 1991, 30, 931; b) N. Sträter, W. N. Lipscomb, T. Klabunde, B. Krebs, ibid. 1996, 108, 2158 and 1996, 35, 2024.
182. Reviews: a) A. D. Ryabov, Angew. Chem. 1991, 103, 945; Angew. Chem. Int. Ed. Engl. 1991, 30, 931; b) N. Sträter, W. N. Lipscomb, T. Klabunde, B. Krebs, ibid. 1996, 108, 2158 and 1996, 35, 2024.
183. Reviews: a) A. D. Ryabov, Angew. Chem. 1991, 103, 945; Angew. Chem. Int. Ed. Engl. 1991, 30, 931; b) N. Sträter, W. N. Lipscomb, T. Klabunde, B. Krebs, ibid. 1996, 108, 2158 and 1996, 35, 2024.
184. Short review: C. Bolm, F. Bienewald, A. Seger, Angew. Chem. 1996, 108, 1767; Angew. Chem. Int. Ed. Engl. 1996, 35, 1656.
185. Short review: C. Bolm, F. Bienewald, A. Seger, Angew. Chem. 1996, 108, 1767; Angew. Chem. Int. Ed. Engl. 1996, 35, 1656.
186. a) K. T. Wan, M. E. Davis, Nature 1994, 370, 449; Aqueous Organometallic Chemistry and Catalysis (Eds.: I. T. Horváth, F. Joó), Kluwer, Dordrecht, 1995;
187. a) K. T. Wan, M. E. Davis, Nature 1994, 370, 449; Aqueous Organometallic Chemistry and Catalysis (Eds.: I. T. Horváth, F. Joó), Kluwer, Dordrecht, 1995;
188. b) M. Sawamura, K. Kitayama, Y. Ito, Tetrahedron: Asymmetry 1993, 4, 1529.
189. T. Shibata, K. Choji, H. Morioka, T. Hayase, K. Soai, Chem. Commun. 1996, 751.
190. D. Astruc in ref. [26a], chap. 3.2.8, p. 915.
191. D. Astruc, Electron Transfer and Radical Processes in Transition Metal Chemistry, VCH, Weinheim, 1995.
192. G. W. Parshall, S. D. Ittel, Homogeneous Catalysis, 2nd ed., Wiley, New York, 1992.
193. a) K. Eller, H. Schwarz, Chem. Rev. 1991, 91, 1121;
194. b) B. S. Freiser, Acc. Chem. Res. 1994, 27, 353;
195. c) D. Schröder, H. Schwarz, Angew. Chem. 1995, 107, 1973; Angew. Chem. Int. Ed. Engl. 1995, 34, 2126;
196. c) D. Schröder, H. Schwarz, Angew. Chem. 1995, 107, 1973; Angew. Chem. Int. Ed. Engl. 1995, 34, 2126;
197. d) H. H. Cornehl, G. Hornung, H. Schwarz, J. Am. Chem. Soc. 1996, 118, 9960;
198. e) A. Fiedler, I. Kretzschmar, D. Schröder, H. Schwarz, ibid. 1996, 118, 9941.
199. B. Brielbeck, E. Spika, M. Frede, E. Steckhan, Bioforum 1994, 17, 22.
200. a) R. A. Lerner, S. J. Benkovic, P. G. Schultz, Science 1991, 252, 659;
201. b) J. D. Stewart, L. J. Liotta, S. J. Benkovic, Acc. Chem. Res. 1993, 26, 396;
202. c) B. L. Iverson, Chemtech 1995, 25, 17;
203. d) E. Keinan, S. C. Sinha, D. Shabat, H. Itzhaky, J.-L. Reymond, Abstr. Pap. 9th Int. Symp. Homogen. Catal., Jerusalem (Israel), 1994, p. 383.
204. a) K. Drauz, H. Waldmann, B. Sauerbrei in ref. [26a], chap. 3.2.1, p. 768;
205. b) Enzyme Catalysis in Organic Synthesis (Eds.: K. Drauz, H. Waldmann), VCH, Weinheim, 1995.
206. a) C. G. Hill, Activation and Functionalization of Alkanes, Wiley, New York, 1989;
207. b) R. G. Bergman, ACS Adv. Chem. Ser. 1992, 230, 211;
208. c) R. H. Crabtree, Chem. Rev. 1995, 95, 987.
209. 1 Synthetic Unit: Activation by Transition-Metal Complexes": A. Behr, Angew. Chem. 1988, 100, 681;
210. Angew. Chem. Int. Ed. Engl. 1988, 27, 661.
211. Monographs: a) A. Behr, Carbon Dioxide Activation by Metal Complexes. VCH, Weinheim, 1988;
212. 1-Chemistry (Ed.: W. Keim), Reidel, Dordrecht, 1983.
213. a) R. G. Bergman, B. A. Arndtzen, Science 1995, 270, 1970;
214. b) P. L. Watson, G. W. Parshall, Acc. Chem. Res: 1985, 18, 51; c) M. Gozin, A. Weisman, Y. Ben-David, D. Milstein, Nature 1993, 364, 699; see also W. D. Jones, ibid. 1993, 364, 676;
215. b) P. L. Watson, G. W. Parshall, Acc. Chem. Res: 1985, 18, 51; c) M. Gozin, A. Weisman, Y. Ben-David, D. Milstein, Nature 1993, 364, 699; see also W. D. Jones, ibid. 1993, 364, 676;
216. b) P. L. Watson, G. W. Parshall, Acc. Chem. Res: 1985, 18, 51; c) M. Gozin, A. Weisman, Y. Ben-David, D. Milstein, Nature 1993, 364, 699; see also W. D. Jones, ibid. 1993, 364, 676;
217. d) M. Gozin, M. Aizenberg, S.-Y. Liou, A. Weisman, J. Ben-David, D. Bilsten, ibid. 1994, 370, 42;
218. e) S.-Y. Liou, M. Gozin, D. Milstein, J. Am. Chem. Soc. 1995, 117, 9774;
219. f) M. Hudlicky, Chemistry of Organic Fluorine Compounds, 2nd ed., Prentice-Hall, New York, 1992, p. 175;
220. g) M. Aizenberg, D. Milstein, Science 1994, 265, 359;
221. h) M. Aizenberg, D. Milstein, J. Am. Chem. Soc. 1995, 117, 8674;
222. i) J.-M. Basset, V. Dufaud, unpublished results;
223. k) J. Corker, F. Lefevre, C. Lécuyer, V. Dufaud, F. Quignard, A. Choplin, J. Evans, J.-M. Basset, Science 1996, 271, 966;
224. l) J.-M. Basset, V. Dufaud, Fr-A 9508552, 1995.
225. M. Tanaka, T. Sakakura, Adv. Chem. Ser. 1992, 230, 181.
226. J. J. Schneider, Angew. Chem. 1996, 108, 1132; Angew. Chem. Int. Ed. Engl. 1996, 35, 1068.
227. J. J. Schneider, Angew. Chem. 1996, 108, 1132; Angew. Chem. Int. Ed. Engl. 1996, 35, 1068.
228. a) E. J. Roskamp, S. F. Pedersen, J. Am. Chem. Soc. 1987, 109, 3152; ibid. 1987, 109, 6551;
229. a) E. J. Roskamp, S. F. Pedersen, J. Am. Chem. Soc. 1987, 109, 3152; ibid. 1987, 109, 6551;
230. b) J. B. Hartung, Jr., S. F. Pedersen, ibid. 1989, 111, 5468.
231. a) H. B. Kagan, J. L. Namy. Tetrahedron 1986, 42, 6573;
232. b) H. B. Kagan, New J. Chem. 1990, 14, 453;
233. c) J. A. Soderquist, Aldrichimica Acta 1991, 24, 24;
234. d) G. A. Molander, Chem. Rev. 1992, 92, 29.
235. See also H. B. Kagan, Bull. Soc. Chim. Fr. 1988, 846.
236. a) W. A. Herrmann in ref. [26a], chap. 3.2.10, p. 948;
237. b) A. Fürstner. A. Hupperts, J. Am. Chem. Soc. 1995, 117, 4468.
238. A. Fürstner, N. Shi, J. Am. Chem. Soc. 1996, 118, 2533.
239. S. Onozawa, T. Sakakura, M. Tanaka. M. Shiro, Tetrahedron 1996, 52. 4291.
240. a) R. A. Sheldon, Top. Curr. Chem. 1993, 164, 21;
241. b) Chemtech 1991, 566;
242. c) R. A. Sheldon, J. Dakka, Catal. Today 1994, 19, 215;
243. d) W. A. Hermann, W. Adam, R. W. Fischer, J. Lin, C. R. Saha-Möller, J. D. G. Correia (Hoechst AG), DE-A 4419 799, 1994 [Chem. Abstr. 1995, 123, 285566g]: EP-A 665209, 1994;
244. e) W. A. Herrmann, W. Adam, J. Lin, C. R. Saha-Möller, R. W. Fischer, J. D. G. Correia, Angew. Chem. 1994, 106, 2545; Angew. Chem. Int. Ed. Engl. 1994, 33, 2475;
245. e) W. A. Herrmann, W. Adam, J. Lin, C. R. Saha-Möller, R. W. Fischer, J. D. G. Correia, Angew. Chem. 1994, 106, 2545; Angew. Chem. Int. Ed. Engl. 1994, 33, 2475;
246. f) W. Adam, W. A. Herrmann, C. R. Saha-Möller, M. Shimizu, J. Mol. Catal. 1995, 97, 15.
247. Monographs: a) Catalytic Oxidations with Hydrogen Peroxide as Oxidant (Ed.: G. Strukul), Kluwer, Dordrecht, 1992;
248. b) L. I. Simandi, Catalytic Activation of Dioxygen by Metal Complexes. Kluwer, Dordrecht, 1992;
249. c) R. A. Sheldon, J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, London, 1981;
250. d) The Activation of Dioxygen and Homonuclear Catalytic Oxidation (Eds.: D. H. R. Barton, A. E. Martell, D. T. Sawyer), Plenum, New York, 1993.
251. a) Anonymus, Chemtech 1996, 26, 3; see also T. R. Boehlow, C. D. Spilling, Tetrahedron Lett. 1996, 37, 2717;
252. a) Anonymus, Chemtech 1996, 26, 3; see also T. R. Boehlow, C. D. Spilling, Tetrahedron Lett. 1996, 37, 2717;
253. b) R. W. Murray, K. Iryanar, J. Chen, J. T. Wearing, J. Org. Chem. 1996, 61, 8099.
254. a) R.Taube in ref. [26a], chap. 2.7, p. 507;
255. b) T. Prinz, W. Keim, B. Driessen-Hölscher, Angew. Chem. 1996, 108, 1835; Angew. Chem. Int. Ed. Engl. 1996, 35, 1708.
256. b) T. Prinz, W. Keim, B. Driessen-Hölscher, Angew. Chem. 1996, 108, 1835; Angew. Chem. Int. Ed. Engl. 1996, 35, 1708.
257. See for example C. Botteghi, G. Del Ponte, M. Narchetti, S. Paganelli, J. Mol. Catal. 1994, 93, 1.
258. a) J.-L. Couturier, C. Paillet, M. Leconte, J.-M. Basset, K. Weiss, Angew. Chem. 1992, 104, 622; Angew. Chem. Int. Ed. Engl. 1992, 31, 628;
259. a) J.-L. Couturier, C. Paillet, M. Leconte, J.-M. Basset, K. Weiss, Angew. Chem. 1992, 104, 622; Angew. Chem. Int. Ed. Engl. 1992, 31, 628;
260. b) J.-L. Couturier, K. Tanaka, M. Leconte, J.-M. Basset, ibid. 1993, 105, 99 and 1993, 32, 112.
261. b) J.-L. Couturier, K. Tanaka, M. Leconte, J.-M. Basset, ibid. 1993, 105, 99 and 1993, 32, 112.
262. a) E. Drent (Shell), EP-A 121 965, 1984 [Chem. Abstr. 1985, 102, 46423];
263. b) E. Drent, J. A. M. van Broekhoven, M. J. Doyle, J. Organomet. Chem. 1991, 417, 235;
264. c) K. Nozaki, N. Sato, H. Takaya, J. Am. Chem. Soc. 1995, 117, 9911;
265. d) E. Drent, P. Arnoldy, P. H. M. Budzelaar, J. Organomet. Chem. 1994, 475, 57;
266. e) ibid. 1994, 475, 75.
267. a) G. W. Parshall, S. D. Ittel, Homogeneous Catalysis, 2nd ed., Wiley, New York, 1992, p. 123;
268. b) B. Cornils, H. Bahrmann, Chemiker-Ztg. 1980, 104, 39;
269. c) J. F. Knifton, Catal. Today 1993, 18, 355.
270. a) M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824;
271. b) U. Koert, Nachr. Chem. Tech. Lab. 1995, 43, 1068.
272. G. Dyker, Angew. Chem. 1995, 107, 2407; Angew. Chem. Int. Ed. Engl. 1995, 34, 2223.
273. G. Dyker, Angew. Chem. 1995, 107, 2407; Angew. Chem. Int. Ed. Engl. 1995, 34, 2223.
274. E. Montffier, G. Fremy, Y. Castanet, A. Mortreux, Angew. Chem. 1995, 107, 2450; Angew. Chem. Int. Ed. Engl. 1995, 34, 2269.
275. E. Montffier, G. Fremy, Y. Castanet, A. Mortreux, Angew. Chem. 1995, 107, 2450; Angew. Chem. Int. Ed. Engl. 1995, 34, 2269.
276. a) C. J. Li, Tetrahedron Lett. 1995, 36, 517;
277. b) R. Sjöholm, R. Rairama, M. Ahonen, J. Chem. Soc. Chem. Commun. 1994, 1217.
278. B. M. Novak in ref. [26a], chap. 3.3.10.1, p. 1132.
279. F. Küber in ref. [26a], chap. 3.4.6, p. 893.
280. H. Sinn, W. Kaminsky, Adv. Organomet. Chem. 1980, 18, 99, and references therein.
281. Review and monograhps: a) H. H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. Waymouth, Angew. Chem. 1995, 107, 1255; Angew. Chem. Int. Ed. Engl. 1995, 34, 143;
282. Review and monograhps: a) H. H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. Waymouth, Angew. Chem. 1995, 107, 1255; Angew. Chem. Int. Ed. Engl. 1995, 34, 143;
283. b) H. Cherdron, M.-J. Brekner, F. Osan, Angew. Makromol. Chem. 1994, 223, 121;
284. c) Ziegler Catalysis (Eds.: G. Fink, R. Mülhaupt, H. H. Brintzinger), Springer, New York, 1995.
285. a) F. Küber, New Sci. 1993, 139(1886), 28;
286. b) F. Küber, M. Aulbach, Chem. Unserer Zeit 1994, 28, 197.
287. a) W. A. Herrmann, W. Baratta, E. Herdtweck, Angew. Chem. 1996, 108, 2098; Angew. Chem. Int. Ed. Engl. 1996, 35, 1951;
288. a) W. A. Herrmann, W. Baratta, E. Herdtweck, Angew. Chem. 1996, 108, 2098; Angew. Chem. Int. Ed. Engl. 1996, 35, 1951;
289. b) W. A. Herrmann, J. Eppinger, R. Anwander, O. Runte, M. Spiegier, Organometallics 1997, in press;
290. c) J. Eppinger, Diplomarbeit, Technische Universität München, 1996;
291. d) W. A. Herrmann, H. Baratta, M. J. A. Morawietz, J. Organomet. Chem. 1995, 497, C4;
292. e) W. A. Herrmann, W. Baratta, ibid. 1996, 506, 357;
293. f) O. Runte, T. Priermeier, R. Anwander, Chem. Commun. 1996, 1385.
294. a) G. W. Coates. R. M. Waymouth, Science 1995, 267, 217.
295. O. Nuyken, et al. unpublished results.
296. W. A. Herrmann in ref. [26a], chap. 3.1.6, p. 712.
297. a) W. A. Herrmann, S. Bogdanovic, R. Poli, T. Priermeier, J. Am. Chem. Soc. 1994, 116, 4989;
298. b) S. Bogdanovic, Ph.D. thesis, Technische Universität München (Germany), 1994.
299. a) R. R. Schrock, Pure Appl. Chem. 1994, 66, 1447;
300. b) O. Fujimura, R. H. Grubbs. J. Am. Chem. Soc. 1996, 118, 2499; C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376.
301. b) O. Fujimura, R. H. Grubbs. J. Am. Chem. Soc. 1996, 118, 2499; C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376.
302. b) O. Fujimura, R. H. Grubbs. J. Am. Chem. Soc. 1996, 118, 2499; C. M. Huwe, J. Velder, S. Blechert, Angew. Chem. 1996, 108, 2542; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376.
303. K. A. Ostoja-Starzewski in ref. [108c], p. 497.
304. L. K. Johnson, C. M. Killian, M. Brookhart, J. Am. Chem. Soc. 1995, 117, 6414.
305. L. K. Johnson, S. Mecking, M. Brookhart, J. Am. Chem. Soc. 1996, 118, 267.
306. J. Haggin, Chem. Eng. News 1996, 74(6), 6.
307. Alkyne polymerization: K. A. Ostoja-Starzewski in Transition Metal Carbyne Complexes (Eds.: F. R. Kreißl et al.), Kluwer, Amsterdam, 1993, p. 67.
308. B. Mohr, D. M. Lynn, R. H. Grubbs, Organometallics 1996, 15, 4317.
309. J. D. Scollard, D. H. McConville, J. Am. Chem. Soc. 1996, 118, 10008.
310. a) Ref.[46a], chap. 2.5;
311. b) Review: F. Agbosson, J.-F. Carpentier, A. Mortreux, Chem. Rev. 1995, 95, 2485;
312. c) M. Baerns in Handbook of Heterogeneous Catalysis (Eds.: G. Ert,. H. Krözinger, J. Weitkamp), Wiley-VCH, Weinheim, 1997.
313. a) R. R. Bader, P. Baumeister, H.-U. Blaser, Chimia 1996, 50, 99;
314. b) P. Baumeister, G. Seifert, H. Steiner (Ciba-Geigy AG), EP-A 584043, 1992 [Chem. Abstr. 1994, 120, 322928n];
315. c) P. Baumeister, W. Meyer, K. Oertle, G. Seifert, U. Siegrist, H. Steiner, presented at the 4th Int. Symp. Heterogen. Catal. Fine Chem. 1996; Stud. Surf. Sci. Catal. 1997, in press.
316. c) P. Baumeister, W. Meyer, K. Oertle, G. Seifert, U. Siegrist, H. Steiner, presented at the 4th Int. Symp. Heterogen. Catal. Fine Chem. 1996; Stud. Surf. Sci. Catal. 1997, in press.
317. a) B. Cornils, W. A. Herrmann in ref. [26a], chap. 1, p. 1, and references therein;
318. b) Review: R. Noyori, Science 1990, 248, 1194; R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345.
319. b) Review: R. Noyori, Science 1990, 248, 1194; R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345.
320. M. J. Cannarsa, Chem. Ind. 1996, 10, 374.
321. J. McGarrity, F Spindler, R. Fuchs, M. Eyer (Lonza AG), EP-A 624587-A2, 1995 [Chem. Abstr. 1995, 122, P81369q].
322. A. Togni, Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475.
323. A. Togni, Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475.
324. a) F. Spindler, B. Pugin, H.-P. Jalett, H.-P. Buser, W. Pittelkow, H.-U. Blaser in Catalysis of Organic Reactions (Ed.: R. E. Malz), Marcel Dekker, New York, 1996, p. 153;
325. b) F. Spindler, B. Pugin (Ciba-Geigy AG), EP-A 0256982, 1988 [Chem. Abstr. 1990, 112, 138725e];
326. c) R. R. Bader, H.-U. Blaser, presented at the 4th Int. Symp. Heterogen. Catal. Fine Chem. 1996; Stud. Surf. Sci. Catal. 1997, in press.
327. c) R. R. Bader, H.-U. Blaser, presented at the 4th Int. Symp. Heterogen. Catal. Fine Chem. 1996; Stud. Surf. Sci. Catal. 1997, in press.
328. a) J. Haber, H. J. Kleiner (Hoechst AG), DE-19527118.1 and DE-19535528.8-43, 1995;
329. II-TPPTS complexes: W. A. Herrmann, J. A. Kulpe, H. Bahrmann, W. Konkol. J. Organomet. Chem. 1990, 389, 35; W. A. Herrmann, J. Kellner, H. Riepl. ibid. 1990, 389, 103; W. A. Herrmann, J. Kulpe, H. Kellner, H. Riepl (Hoechst AG), DE-3840600, 1988 [Chem. Abstr. 1991, 114, 43174z]; EP-0372313, 1997;
330. II-TPPTS complexes: W. A. Herrmann, J. A. Kulpe, H. Bahrmann, W. Konkol. J. Organomet. Chem. 1990, 389, 35; W. A. Herrmann, J. Kellner, H. Riepl. ibid. 1990, 389, 103; W. A. Herrmann, J. Kulpe, H. Kellner, H. Riepl (Hoechst AG), DE-3840600, 1988 [Chem. Abstr. 1991, 114, 43174z]; EP-0372313, 1997;
331. II-TPPTS complexes: W. A. Herrmann, J. A. Kulpe, H. Bahrmann, W. Konkol. J. Organomet. Chem. 1990, 389, 35; W. A. Herrmann, J. Kellner, H. Riepl. ibid. 1990, 389, 103; W. A. Herrmann, J. Kulpe, H. Kellner, H. Riepl (Hoechst AG), DE-3840600, 1988 [Chem. Abstr. 1991, 114, 43174z]; EP-0372313, 1997;
332. c) J. A. Kulpe, Ph.D. thesis. Technische Universität München (Germany), 1989;
333. J. Kellner, Ph.D. thesis, Technische Universität München, 1989;
334. C. W. Kohlpaintner, Ph.D. thesis, Technische Universität München, 1992;
335. d) W. A. Herrmann in ref. [26a], pp. 712-732;
336. e) W. A. Herrmann, C. Brossmer, M. Beller, H. Fischer (Hoechst AG), DE-4.421.730, DE-4.421.753, 1994.
337. H.-U. Blaser, H.-P. Jalett, F. Spindler, J. Mol. Catal. 1996, 107, 85.
338. H.-U. Blaser, B. Pugin, Chiral Reactions in Heterogeneous Catalysis, Plenum, New York, 1995, p. 33.
339. C. P. Snow, The Two Cultures: And a Second Look, Cambridge University Press, London, 1959.