The metathesis reactions: From a historical perspective to recent developments

New Journal of Chemistry

Volumn 29, Issue 1, 2005, Pages 42-56

  Astruc, Didier ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; CYCLOBUTANE; FUNCTIONAL GROUP; METAL COMPLEX; METALLACYCLOBUTANE; ORGANIC COMPOUND; ORGANOMETALLIC COMPOUND; POLYMER; UNCLASSIFIED DRUG; WATER;

CATALYST; CATALYST SUPPORT; CHEMICAL REACTION; HISTORY; MATERIALS; METATHESIS REACTION; ORGANIC CHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW; SYNTHESIS;

EID: 13244289910     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b412198h     Document Type: Review

References (217)

1. (a) Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vols. 1-3: Catalyst Development (vol. 1); Applications in Organic Synthesis (vol. 2); Applications in Polymer Synthesis (vol. 3);
2. (a) Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vols. 1-3: Catalyst Development (vol. 1); Applications in Organic Synthesis (vol. 2); Applications in Polymer Synthesis (vol. 3);
3. (a) Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vols. 1-3: Catalyst Development (vol. 1); Applications in Organic Synthesis (vol. 2); Applications in Polymer Synthesis (vol. 3);
4. (a) Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vols. 1-3: Catalyst Development (vol. 1); Applications in Organic Synthesis (vol. 2); Applications in Polymer Synthesis (vol. 3);
5. (b) For a major account of Ru metathesis catalysts, see: S. T. Nguyen and T. M. Trnka, in Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 1, ch. 1.6;
6. T. M. Trnka and R. H. Grubbs, Acc. Chem. Res., 2001, 34, 18 (this article also contains many references to reviews);
7. For mechanistic aspects of Ru metathesis catalysts, see M. S. Sanford and J. Love, in Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 1, ch. 1.9;
8. (e) R. H. Grubbs, Tetrahedron, 2004, 60, 7117 (this review article also contains the references to more than 400 Grubbs' articles);
9. (f) R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413.
10. (a) R. R. Schrock, J. Mol. Cat. A, 2004, 213, 21;
11. (b) R. R. Schrock and A. H. Hoveyda, Angew. Chem., Int. Ed., 2003, 42, 4592;
12. R. R. Schrock, Chem. Rev., 2002, 102, 145;
13. R. R. Schrock, Top. Organomet. Chem., 1998, 1, 1;
14. (e) R. R. Schrock, Tetrahedron, 1999, 55, 8141;
15. (f) R. R. Schrock, in Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 1. ch. 1.3 and 1.11.
16. (a) K. J. Ivin and J. C. Mol, Olefin Metathesis and Metathesis Polymerization, Academic Press, New York, 1997;
17. (b) J. C. Mol, J. Mol. Cat. A, 2004, 213, 39;
18. J. C. Mol, Top. Catal., 2004, 27, 95.
19. (a) C. Copéret, M. Chabanas, R. Petroff Saint-Arroman and J.-M. Basset, Angew. Chem., Int. Ed., 2003, 42, 156;
20. (b) C. Copéret, F. Lefebvre, J.-M. Basset, Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 1, ch. 1.4 and 1.12;
21. C. Copéret, New J. Chem., 2004, 28, 1.
22. (a) A. Fürstner, Angew. Chem., Int. Ed., 2000, 39, 3012 (review);
23. (b) Alkene Metathesis in Organic Chemistry, ed. A. Fürstner, Springer, Berlin, 1998;
24. A. Fürstner, Top. Organomet. Chem., 1998, 1, 37;
25. A. Fürstner, Top. Catal., 1997, 36, 2037;
26. (e) A. Fürstner, L'Actualité Chimique, 2003, 4-5, 57;
27. (f) For a review on alkyne metathesis, see: A. Fürstner, in Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 2, ch. 2.12.
28. (a) Reviews on cross metathesis: S. J. Connor and S. Blechert, Angew. Chem., Int. Ed., 2003, 42, 1900;
29. (b) M. Schuster and S. Blechert, Angew. Chem,. Int. Ed. Engl., 1997, 36, 2036;
30. For a review on tandem ring closing metathesis, see: S. Randl and S. Blechert, in Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 2, ch. 2.
31. (a) For reviews on metathesis polymerization, see: M. R. Buchmeiser, Chem. Rev., 2000, 100, 1565 and M. R. Buchmeiser, in Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 3, ch. 3.7;
32. (a) For reviews on metathesis polymerization, see: M. R. Buchmeiser, Chem. Rev., 2000, 100, 1565 and M. R. Buchmeiser, in Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 3, ch. 3.7;
33. (b) For a review on supported metathesis catalysts, see: M. R. Buchmeiser, New J. Chem., 2004, 28, 549;
34. For reviews on metathesis polymerization, see the Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 3, ch. 11.
35. A. H. Hoveyda, D. G. Gillingham, J. J. Van Veldhuizen, O. Kataoka, S. B. Garber, J. S. Kingsbury and J. P. A. Harrity, Org. Biol. Chem., 2004, 2, 8 (review); see also ref. 2b.
36. (a) A. Deithers and S. F. Martin, Chem. Rev., 2004, 104, 2199 (heterocycle synthesis);
37. (b) For applications of ring-closing metathesis to alkaloid synthesis, see: S. F. Martin in Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 2, ch. 2.9. For other applications of metathesis to organic synthesis, see the Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 3, ch. 14.
38. (b) For applications of ring-closing metathesis to alkaloid synthesis, see: S. F. Martin in Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 2, ch. 2.9. For other applications of metathesis to organic synthesis, see the Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 3, ch. 14.
39. (a) D. Evans, J. A. Osborn, F. H. Jardine and G. Wilkinson, Nature (London), 1965, 208, 1203;
40. (b) H. Kagan and T. P. Dang, J. Chem. Soc., Chem. Commun., 1971, 481;
41. H. Kagan and T. P. Dang, J. Am. Chem. Soc., 1972, 94, 6429.
42. A. Loupy, B. Tchoubar and D. Astruc, Chem. Rev., 1992, 92, 1141.
43. (a) N. Calderon, Tetrahedron Lett., 1967, 34, 3327;
44. (b) N. Calderon, Acc. Chem. Res., 1972, 5, 127.
45. (a) R. L. Banks and G. C. Bailey, Int. Eng. Prod. Dev., 1964, 3, 170;
46. (b) For a historical account of the early days, see: H. S. Eleuterio, J. Mol. Catal., 1991, 65, 55 (in particular, compare ref. 13c and 13d);
47. H. S. Eleuterio, German Pat. 1072811, 1960;
48. W. L. Truett, D. R. Johnson, I. M. Robinson and B. P. Montague, J. Am. Chem. Soc., 1960, 82, 2337;
49. (e) M. R. Rouhi, Chem. Eng. News, 2002, 29 (December 23).
50. (a) M. Blanchard and A. Mortreux, Bull. Soc. Chim., 1972, 4, 1641;
51. (b) M. Blanchard and A. Mortreux, J. Mol. Catal., 1975-6, 1, 101;
52. A. Mortreux, J. C. Delgrange, M. Blanchard and B. Lubochinsky, J. Mol. Catal., 1977, 2, 73;
53. A. Mortreux, F. Petit and M. Blanchard, Tetrahedron Lett., 1978, 49, 4967;
54. 4OH or other activated phenols, see text);
55. (f) U. H. F. Bunz, in Modern Arene Chemistry, ed. D. Astruc, Wiley-VCH, Weinheim, 2002, pp. 217-249;
56. (g) H. H. F. Bunz, in Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 3, eh. 3, 10;
57. (h) K. Grela and J. Ignatowska, Org. Lett., 2002, 4, 3747;
58. A. Michrowska, R. Bujok, S. Harutyunyan, V. Sashuk, G. Dolgonos and K. Grela, J. Am. Chem. Soc., 2004, 126, 9318;
59. (j) V. Huc, R. Weihofen, I. Martin-Jimenez, P. Oulié, C. Lepetit, G. Lavigne and R. Chauvin, New J. Chem., 2003, 27, 1412;
60. (k) W. Zhang, S. Kraft and J. S. Moore, Chem. Commun., 2003, 832;
61. W. Zhang, S. Kraft and J. S. Moore, J. Am. Chem. Soc., 2004, 126, 329;
62. W. Zhang and J. S. Moore, J. Am. Chem. Soc., 2004, 126, 12796.
63. E. O. Fischer, Angew. Chem., Int. Ed. Engl., 1964, 580.
64. G. Natta, Angew. Chem., Int. Ed. Engl., 1964, 3, 723.
65. Y. Chauvin and J.-L. Hérisson, Makromol. Chem., 1971, 141, 161.
66. (a) Y. Chauvin, C. R. Seances Acad. Sci., Ser. C, 1973, 276, 169;
67. (b) Y. Chauvin, D. Commereuc and D. Cruypelinck, Makromol. Chem., 1976, 177, 2637.
68. (a) F. N. Tebbe, G. W. Parshall and G. S. Reddy, J. Am. Chem. Soc., 1978, 100, 3611;
69. (b) T. R. Howard, J. B. Lee and R. H. Grubbs, J. Am. Chem. Soc., 1980, 102, 6876;
70. E. V. Anslyn and R. H. Grubbs, J. Am. Chem. Soc., 1987, 109, 4880;
71. J. M. Hawkins and R. H. Grubbs, J. Am. Chem. Soc., 1988, 110, 2821.
72. (a) C. P. Casey and T. J. Burkhardt, J. Am. Chem. Soc., 1974, 96, 7808;
73. (b) T. J. Katz and S. J. Lee, J. Am. Chem. Soc., 1980, 102, 422;
74. T. J. Katz, Adv. Organomet. Chem., 1978, 16, 283;
75. This alkyne polymerization mechanism (ref. 20b,c) can be considerably accelerated by coupling with electron-transfer-chain catalysis: M.-H. Desbois and D. Astruc, New J. Chem., 1989, 13, 595.
76. (a) G. Wilkinson, Science, 1974, 185, 109;
77. (b) G. Wilkinson, Pure Appl. Chem., 1959, 71, 627;
78. R. R. Schrock and G. W. Parshall, Chem. Rev., 1976, 76, 243;
79. M. F. Lappert and R. Pierce, Chem. Rev., 1976, 76, 219.
80. (a) R. R. Schrock, J. Am. Chem. Soc., 1974, 96, 6796;
81. (b) R. R. Schrock, Acc. Chem. Res., 1979, 12, 98;
82. R. R. Schrock, Science, 1983, 219, 13;
83. J. Feldman and R. R. Schrock, Prog. Inorg. Chem., 1991, 39, 1;
84. (e) R. R. Schrock, S. M. Rocklage, J. H. Wengrovius. G. Rupprecht and J. Feldmann, J. Mol. Catal., 1980, 8, 73;
85. (f) J. H. Wengrovius, R. R. Schrock, M. R. Churchill, J. R. Missert and W. J. Youngs, J. Am. Chem. Soc., 1980, 102, 4515.
86. (a) R. R. Schrock, J. S. Murdzek, G. C. Bazan, J. Robbins, M. DiMare and M. O'Regan, J. Am. Chem. Soc., 1990, 112, 3875;
87. (b) G. C. Bazan, E. Khosravi, R. R. Scrock, W. J. Feast, V. C. Gibson, M. B. O'Regan, J. K. Thomas and W. M. Davis, J. Am. Chem. Soc., 1990, 112, 8378;
88. G. C. Bazan, J. H. Oskam, H. N. Cho, L. Y. Park and R. R. Schrock, J. Am. Chem. Soc., 1991, 113, 6899.
89. R. R. Schrock, S. McLain and J. Sancho, J. Am. Chem. Soc., 1979, 101, 4558.
90. (a) A. Bre, Y. Chauvin and D. Commereuc, Nouv. J. Chim., 1986, 10, 535;
91. (b) Y. Chauvin and H. Olivier, in Applied Homogeneous Catalysis, eds. B. Cornils and W. A. Herrmann, VCH, Weinheim, 1996, vol. 1, ch. 2.3.1 and 2.3.6.
92. (a) J. Kress, M. Wesolek and J. A. Osborn, J. Chem. Soc., Chem. Commun., 1982, 514;
93. (b) J. Kress, M. Wesolek and J. A. Osborn, J. Am. Chem. Soc., 1883, 105, 6346;
94. J. Kress, J. A. Osborn, R. M. E. Green, K. J. Ivin and J. J. Rooney, J. Am. Chem. Soc., 1987, 109, 899;
95. J. Kress, A. Aguero and J. A. Osborn, J. Mol. Catal., 1986, 36, 1.
96. (a) F. Quignard, M. Leconte and J.-M. Basset, J. Chem. Soc., Chem. Commun., 1985, 1816;
97. (b) M. Leconte, J.-M. Basset, F. Quignard and C. Larroche, in Reactions of Coordinated Ligands, ed. P. S. Braterman, Plenum, New York, 1986, vol. 1, pp. 371-420;
98. F. Lefebvre, M. Lecomte, S. Pagano, A. Mutch and J.-M. Basset, Polyhedron, 1995, 14, 3209.
99. (a) J. B. Alexander, D. S. La, D. R. Cefalo, A. H. Hoveyda and R. R. Schrock, J. Am. Chem. Soc., 1998, 120, 4041;
100. (b) S. S. Zu, D. R. Cefalo, D. S. La, J. Y. Jamieson, W. M. Davis, A. H. Hoveyda and R. R. Schrock, J. Am. Chem. Soc., 1999, 121, 8251;
101. S. L. Aeilts, D. R. Cefalo, P. J. Bonitatebus, J. H. Houser, A. H. Hoveyda and R. R. Schrock, Angew. Chem., Int. Ed., 2001, 40, 1452;
102. X. Teng, D. R. Cefalo, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 10779;
103. (e) K. H. Hultzsch, J. A. Jernelius, A. H. Hoveyda and R. R. Schrock, Angew. Chem., Int. Ed., 2002, 114, 609;
104. (f) W. C. P. Tsang, J. A. Jernelius, G. A. Cortez, G. S. Weatherhead, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 2591;
105. (g) W. C. P. Tsang, K. C. Hultzsch, J. B. Alexander, P. J. Bonitatebus and R. R. Schrock, J. Am. Chem. Soc., 2003, 125, 2652.
106. D. Astruc, Chimie Organométallique, EDP Sciences, Les Ulis, 2000, ch. 10 on metal-carbene and carbyne complexes (Spanish version: Reverté, Barcelona, 2004).
107. (a) P. W. Jolly and R. Pettit, J. Am. Chem. Soc., 1966, 88, 5044;
108. (b) V. Guerchais and D. Astruc, J. Chem. Soc., Chem. Commun., 1985, 835.
109. M. L. H. Green, L. C. Mitchard and M. G. Swanwick, J. Chem. Soc. A, 1971, 794.
110. R. H. Grubbs, J. Am. Chem. Soc., 1972, 94, 2538.
111. (a) G. Natta, G. Dall'Asta and L. Porri, Makromol. Chem., 1965, 81, 253;
112. (b) The capture by Grubbs of the renaissance of polymerization chemistry is represented by his review article: R. H. Grubbs and W. J. Tumas, Science, 1989, 243, 907.
113. (a) B. M. Novak and R. H. Grubbs, J. Am. Chem. Soc., 1988, 110, 7542;
114. (b) M. B. France, R. H. Grubbs, V. McGrath and R. A. Paciello, Macromolecules, 1993, 26, 4742;
115. S. T. Nguyen, L. K. Johson, R. H. Grubbs and J. W. Ziller, J. Am. Chem. Soc., 1992, 114, 3974;
116. P. Schwab, M. B. France, J. W. Ziller and R. H. Grubbs, Angew. Chem., Int. Ed. Engl., 1998, 37, 1124;
117. (e) A. Demonceau, A. F. Noels, E. Saive and A. J. Hubert, J. Mol. Catal., 1992, 76, 123;
118. (f) A. W. Stumpf, E. Saive, A. Demonceau and A. F. Noels, J. Chem. Soc., Chem. Commun., 1995, 1127.
119. (a) M. Olivan and K. Caulton, Chem. Commun., 1997, 1733;
120. (b) J. Wolf, W. Stüer, C. Grünwald, H. Werner, P. Schwab and M. Schulz, Angew. Chem., Int. Ed. Engl., 1998, 37, 1124;
121. H. Werner, J. Wolf, in Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 1, ch. 1.8;
122. M. Gandelman, B. Rybtchinski, N. Ashkenazi, R. M. Gauvin and D. Milstein, J. Am. Chem. Soc., 1997, 119, 3887.
123. (a) A. J. Arduengo, Acc. Chem. Res., 1999, 32, 913;
124. (b) W. A. Herrmann and C. Köcher, Angew. Chem., Int. Ed. Engl., 1997, 109, 2256;
125. D. Bourissou, O. Guerret, F. P. Gabbaï and G. Bertrand, Chem. Rev., 2000, 100, 39;
126. T. Wetskamp, W. C. Schattenmann and W. A. Herrmann, Angew. Chem., Int. Ed., 1998, 37, 2490.
127. (a) J. Huang, E. D. Stevens, S. P. Nolan and J. L. Petersen, J. Am. Chem. Soc., 1999, 121, 2647;
128. (b) M. Scholl, T. M. Trnka, J. P. Morgan and R. H. Grubbs, Tetrahedron Lett., 1999, 40, 2247;
129. L. Ackermann, A. Fürstner, T. Weskamp, F. J. Kohl and W. A. Herrmann, Tetrahedron Lett., 1999, 40, 4787;
130. M. Scholl, S. Ding, C. W. Lee and R. H. Grubbs, Org. Lett., 1999, 1, 953;
131. (e) T. M. Trnka, J. P. Morgan, M. S. Sanford, T. E. Wilhelm, M. Scholl, T. L. Choi, S. Ding, M. W. Day and R. H. Grubbs, J. Am. Chem. Soc., 2003, 125, 2546;
132. (f) J. A. Love, M. S. Sanford, M. W. Day and R. H. Grubbs, J. Am. Chem. Soc., 2003, 125, 10103;
133. (g) A. K. Chatterjee, T.-L. Choi, D. P. Sanders and R. H. Grubb, J. Am. Chem. Soc., 2003, 125, 11360 (this article is particularly useful for the selectivity in cross metathesis);
134. (h) C. Morril and R. H. Grubbs, J. Org. Chem., 2003, 68, 603;
135. F. M. Kilbinger, S. J. Candrill, A. W. Waltman, M. W. Day and R. H. Grubbs, Angew. Chem., Int. Ed., 2003, 42, 3281;
136. (j) J. A. Love, J. P. Morgan, T. M. Trnka and R. H. Grubbs, Angew. Chem., Int. Ed., 2003, 42, 4035;
137. (k) The second-generation Grubbs' catalyst thermally decomposes at 55 °C in benzene to give, after 72 h, a 46% isolated yield of a hydridic dinuclear carbyne (HRuCRu) complex that catalyzes olefin isomerization: H. Hong, M. W. Day and R. H. Grubbs, J. Am. Chem. Soc., 2004, 126, 7414.
138. (a) J. S. Kingsbury, J. P. A. Harrity, P. J. Bonitatebus and A. H. Hoveyda, J. Am. Chem. Soc., 1999, 121, 791;
139. (b) K. Grela, S. Harutyunyan and A. Michrowska, Angew. Chem., Int. Ed., 2002, 41, 4038;
140. J. O. Krause, M. T. Zarka, U. Anders, R. Weberskirch, O. Nuyken and M. R. Buchmeiser, Angew. Chem., Int. Ed., 2003, 42, 5965;
141. T. Honda, H. Namiki, K. Kaneda and H. Misutani, Org. Lett., 2004, 6, 87.
142. (a) S. J. Connon, A. Dunne and S. Blechert, Angew. Chem., Int. Ed., 2002, 41, 3835;
143. (b) H. Wakamatsu and S. Blechert, Angew. Chem., Int. Ed., 2002, 41, 2403 (with a biphenyl group, see Fig. 5);
144. H. Wakamatsu and S. Blechert, Angew. Chem.. Int. Ed., 2002, 41, 794 (with a binaphtol group);
145. A. M. Dunne, S. Mix and S. Blechert, Tetrahedron Lett., 2003, 44, 2733 (RCM and ROCM).
146. (a) P. Wijkens, J. T. B. H. Jastrzebski, P. A. van der Schaaf, R. Kolly, A. Hafner and G. van Koten, Org. Lett., 2000, 122, 8168;
147. (b) S. B. Garber, J. S. Kingsbury, B. L. Gray and A. H. Hoveyda, J. Am. Chem. Soc., 2000, 122, 8168.
148. (a) S. M. Hansen, M. A. O. Volland, F. Rominger, F. Eisenträger and P. Hofmann, Angew. Chem., Int. Ed., 1999, 38, 1273;
149. (b) S. M. Hansen, F. Rominger, M. Metz and P. Hofmann, Chem.-Eur. J., 1999, 5, 557;
150. M. A. O. Volland, S. M. Ansen, F. Rominger and P. Hofmann, Organometallics, 2004, 23, 800.
151. C. Six, K. Beck, A. Wegner and W. Leitner, Organometallics, 2000, 19, 4639.
152. (a) A. Fürstner, C. Picquet, C. Bruneau and P. H. Dixneuf, Chem. Commun., 1998, 1315;
153. (b) A. Fürstner, M. Liebl, C. W. Lehmann, M. Picquet, R. Kunz, C. Bruneau, D. Touchard and P. H. Dixneuf, Chem.-Eur. J., 2000, 6, 1847;
154. A. Fürstner, R. Ackermann, B. Gabor, R. Goddart, W. Lehmann, R. Mynott, F. Stelzer and O. R. Thiel, Angew. Chem., Int. Ed., 2001, 7, 3236;
155. A. Fürstner, A. S. Castanet, K. Radkovski and C. W. Lehman, J. Org. Chem., 2003, 68, 1521;
156. (e) J. C. Conrad, D. Amoroso, P. Czechura, G. P. A. Yap and D. E. Fogg, Organometallics, 2003, 22, 3634;
157. (f) J. L. Snelgrove, J. C. Conrad, G. P. A. Yap and D. E. Fogg, Inorg. Chim. Acta, 2003, 345, 268;
158. (g) Ru=CH(SR) catalysts: H. Katayama, M. Nagao and F. Ozawa, Organometallics, 2003, 22, 586;
159. (h) P. A. van der Schaaf, R. Kolly, H.-J. Kirner, F. Rime, A. Mühlebach and A. Hafner, J. Organomet. Chem., 2000, 606, 65;
160. 2 in metathesis catalysis: A. Fürstner, D. Koch, W. Langemann and C. Leitner, Angew. Chem., Int. Ed. Engl., 1997, 36, 2466.
161. (a) A. Demonceau, A. W Stumpf, E. Saive and A. F. Noels, Macromolecules, 1997, 30, 3127;
162. (b) J. Cossy, F. Bargiggia and S. Bouzbouz, Org. Lett., 2003, 5, 459;
163. S. Bouzbouz, E. De Lemos and J. Cossy, Adv. Synth. Catal., 2002, 344, 627;
164. Y. Ki, M. F. Mayer and S. C. Zimmerman, Angew. Chem., Int. Ed., 2003, 42, 1121;
165. (e) R. V. Anana, S. Baktaraman and V. K. Singh, J. Org. Chem., 2003, 68, 3356;
166. (f) J. H. Cho and B. M. Kim, Org. Lett., 2003, 5, 531;
167. (g) D. F. Taber and K. J. Frankowski, J. Org. Chem., 2003, 68, 6047;
168. (h) B. Alcaide and P. Almendros, Chem.-Eur. J., 2003, 9, 1258.
169. (a) S. Gatard, S. Nlate, E. Cloutet, G. Bravic, J.-C. Blais and D. Astruc, Angew. Chem., Int. Ed., 2003, 42, 452;
170. (b) S. Gatard, S. Kahlal, D. Méry, S. Méry, S. Nlate, E. Cloutet, J.-Y. Saillard and D. Astruc, Organometallics, 2004, 23, 1313.
171. (a) M. Lynn, B. Mohr and R. H. Grubbs, J. Am. Chem. Soc., 1998, 120, 1627;
172. (b) D. M. Lynn, B. Mohr, R. H. Grubbs, L. M. Henling and M. W. Day, J. Am. Chem. Soc., 2000, 122, 6601.
173. (a) N. Audic, H. Clavier, M. Mauduit and J.-C. Guillemin, J. Am. Chem. Soc., 2003, 125, 9248;
174. (b) D. Sémeril, H. Olivier-Bourbigou, C. Bruneau and P. H. Dixneuf, Chem. Commun., 2002, 146.
175. (a) V. Martinez, J.-C. Blais and D. Astruc, Org. Lett., 2002, 4, 651;
176. (b) V. Martinez, J.-C. Blais, G. Bravic and D. Astruc, Organometallics, 2004, 23, 861.
177. D. Astruc and F. Chardac, Chem. Rev., 2001, 101, 2991.
178. (a) M. Mori, Top. Organomet., 1998, 1, 133;
179. (b) C. Dietrich-Bucherer, G. Rapenne and J.-P. Sauvage, Chem. Commun., 1997, 2053;
180. T. O. Schrader and M. L. Snapper, in in Handbook of Metathesis, ed. R. H. Grubbs, Wiley-VCH, Weinheim, 2003, vol. 2, ch. 2.6 (review on ring-opening cross metathesis).
181. (a) V. Martinez, J.-C. Blais and D. Astruc, Angew. Chem., Int. Ed., 2002, 42, 2586;
182. (b) A. M. Martin-Alvarez, F. Hampel, A. M. Arif and J. A. Gladysz, Organometallics, 1999, 18, 955;
183. See also: P. L. Ng and J. N. Lambert, Synlett., 1999, 1749.
184. S. D. Burke, N. Müller and C. M. Beaudry, Org. Lett., 1999, 1, 1827.
185. (a) M. Hirama, Science, 2001, 294, 1904;
186. (b) T. Seiders, D. W. Ward and R. H. Grubbs, Org. Lett., 2001, 3, 3225;
187. L. F. Tieze and F. Haunert, in Stimulating Concepts in Chemistry, eds. F. Vögtle, J.F. Stoddart and M. Shibasaki, Wiley-VCH, Weinheim, 2000, pp. 39-64.
188. (a) J. Corker, F. Lefebvre, C. Lecuyer, V. Dufaud, F. Quignard, A. Choplin, J. Evans and J.-M. Basset, Science, 1996, 271, 966;
189. (b) V. Vidal, A. Théollier, J. Thivolle-Cazat and J.-M. Basset, Science, 1997, 276, 99;
190. O. Maury, L. Lefort, V. Vidal, J. Thivolle-Cazat and J.-M. Basset, Angew. Chem., Int. Ed., 1999, 38, 1952;
191. C. Copéret, O. Maury, J. Thivolle-Cazat and J.-M. Basset, Angew. Chem., Int. Ed., 2001, 40, 2331;
192. (e) F. Rataboul, A. Baudouin, C. Thieuleux, L. Veyre, C. Copéret, J. Thivolle-Cazat, J.-M. Basset, A. Lesage and L. Emsley, J. Am. Chem. Soc., 2004, 126, 12541;
193. (f) E. Le Roux, M. Chabanas, A. Baudouin, A. de Mallmann, C. Copétet, E. A. Quadrelli, J. Thivolle-Cazat, J.-M. Basset, W. Lukens, A. Lesage, L. Emsley and G. Sunley, J. Am. Chem. Soc., 2004, 126, 13391;
194. 0 complexes, see: D. Soulivong, C. Copéret, J. Thivolle-Cazat, J.-M. Basset, B. M. Maunderf, R. Pardi and G. Sunley, Angew. Chem., Int. Ed., 2004, 43, 5366;
195. 2);
196. 4).
197. R. R. Schrock, D. N. Clark, J. Sancho, J. H. Wengrovius and S. F. Pederson, Organometallics, 1982, 1, 1645.
198. (a) A. Fürstner, C. Mathes and C. W. Lehmann, J. Am. Chem. Soc., 1999, 121, 9453;
199. (b) A. Fürstner, C. Mathes and C. W. Lehmann, Chem.-Eur. J., 2001, 7, 5299;
200. A. Fürstner, A.-S. Castanet, K. Radkowski and C. W. Lehmann, J. Org. Chem., 2003, 68, 1521;
201. O. S. Miljanic, K. P. C. Vollhardt and G. D. Whitener, Synlett., 2003, 29.
202. R. Petroff Saint-Aroman, M. Chabanas, C. Copéret, J.-M. Basset and L. Emsley, J. Am. Chem. Soc., 2001, 123, 3820.
203. D. M. Lynn, B. Mohr and R. H. Grubbs, J. Am. Chem. Soc., 1998, 120, 1627.
204. (a) J. O. Krause, M. T. Zarka, U. Anders, R. Weberkirch, O. Nuyken and M. Buchmeiser, Angew. Chem., Int. Ed., 2003, 42, 5965;
205. (b) M. T. Zarka, O. Nuyken and R. Weberskirch, Macromol. Rapid Commun., 2004, 25, 858.
206. N. E. Leadbeater and M. Marco, Chem. Rev., 2002, 102, 3217.
207. M. Chabanas, A. Baudouin, C. Copéret and J.-M. Basset, J. Am. Chem. Soc., 2003, 125, 492.
208. (a) W. A. Herrmann, A. W. Stumpf, T. Priermeier, S. Bogdanovic, V. Dufaud and J.-M. Basset, Angew. Chem., Int. Ed. Engl., 1996, 35, 2803;
209. (b) R. Petroff Saint-Aroman, M. Chabanas, C. Copéret, J.-M. Basset and L. Emsley, J. Am. Chem. Soc., 2001, 123, 3820.
210. (a) Synthesis of medium-sized rings by RCM: M. E. Maier, Angew. Chem., Int. Ed., 2000, 39, 2073;
211. (b) Extensive review on ring synthesis by RCM: K. C. Nicolaou, N. P. King and Y. He, Top. Organomet. Chem., 1998, 1, 73.
212. M. H. D. Postema, J. L. Piper, V. Komanduri and L. Liu, Angew. Chem., Int. Ed., 2004, 43, 2915.
213. (a) M. T. Reetz, Comp. Coord. Chem. II, 2004, 9, 509;
214. (b) A. D. Piscopio and J. E. Robinson, Curr. Opin. Chem. Biol., 2004, 8, 245;
215. B. Schmidt, Eur. J. Org. Chem., 2004, 1865.
216. (a) A. Carrillo and R. Cane, J. Polym. Sci., Part A: Polym. Chem., 2004, 42, 3352;
217. (b) V. Lapinte, P. de Frémont, V. Montembault and L. Fontaine, Macromol. Chem. Phys., 2004, 205, 1238.