Synthesis and activity of ruthenium alkylidene complexes coordinated with phosphine and N-heterocyclic carbene ligands

Journal of the American Chemical Society

Volumn 125, Issue 9, 2003, Pages 2546-2558

  Trnka, Tina M ^a   Morgan, John P ^a   Sanford, Melanie S ^a   Wilhelm, Thomas E ^a   Scholl, Matthias ^a   Choi, Tae Lim ^a   Ding, Sheng ^a   Day, Michael W ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS;

ALCOHOLS; CRYSTAL STRUCTURE; HYDROGEN BONDS; OLEFINS; SYNTHESIS (CHEMICAL);

RUTHENIUM COMPOUNDS;

ALCOHOL; ALKENE; CARBENOID; CHLOROFORM; COORDINATION COMPOUND; HETEROCYCLIC COMPOUND; LIGAND; PHOSGENE; PHOSPHINE DERIVATIVE; RUTHENIUM COMPLEX;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CRYSTAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

ALKENES; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS; HYDROCARBONS; IMIDAZOLES; LIGANDS; METHANE; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PHOSPHINES; RUTHENIUM; TRIAZOLES;

EID: 0037420362     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021146w     Document Type: Article

References (177)

1. Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974-3975.
2. (a) Rölle, T.; Grubbs, R. H. Chem. Commun. 2002. 1070-1071.
3. (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
4. (c) Sanford, M. S.; Henling, L. M.; Day, M. W.; Grubbs, R. H. Angew. Chem., Int. Ed. 2000, 39, 3451-3453.
5. (d) Bielawski, C. W.; Louie, J.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 12872-12873.
6. (e) Ulman, M.; Belderrain, T. R.; Grubbs, R. H. Tetrahedron Lett. 2000, 41, 4689-4693.
7. (f) Lynn, D. M.; Mohr, B.; Grubbs, R. H.; Henling, L. M.; Day, M. W. J. Am. Chem. Soc. 2000, 122, 6601-6609.
8. (g) Dias, E. L.; Grubbs, R. H. Organometallics 1998, 17, 2758-2767.
9. (h) Sanford, M. S.; Henling, L. M.; Grubbs, R. H. Organometallics 1998, 77, 5384-5389.
10. (i) Chang, S.; Jones, L.; Wang, C.; Henling, L. M.; Grubbs, R. H. Organometallics 1998, 17, 3460-3465.
11. (j) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887-3897.
12. (k) Wilhelm, T. E.; Belderrain, T. R.; Brown, S. N.; Grubbs, R. H. Organometallics 1997, 16, 3867-3869.
13. (l) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
14. (m) Wu, Z.; Nguyen, S. T. Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 5503-5511.
15. (n) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
16. (o) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858-9859.
17. Representative homogeneous examples: (a) Stüer, W.; Wolf, J.; Werner, H. J. Organomet. Chem. 2002. 641, 203-207.
18. (b) Buchowicz, W.; Ingold, F.; Mol, J. C.; Lutz, M.; Spek, A. L. Chem.-Eur. J. 2001, 7, 2842-2847.
19. (c) Coalter, J. N.; Caulton, K. G. New J. Chem. 2001, 25, 679-684.
20. (d) Nieczypor, P.; van Leeuwen, P. W. N. M.; Mol, J. C.; Lutz, M.; Spek, A. L. J. Organomet. Chem. 2001, 625, 58-66.
21. (e) Fürstner, A.; Guth, O.; Düffels, Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem.-Eur. J. 2001, 7, 4811-4820.
22. (f) Amoroso, D.; Fogg, D. E. Macromolecules 2000, 33, 2815-2818.
23. (g) Werner, H.; Jung, S.; González-Herrero, P.; Ilg, K.; Wolf, J. Eur. J. Inorg. Chem. 2001, 1957-1961.
24. (h) Leung, W.-H.; Lau, K.-K.; Zhang, Q.-F.; Wong, W.-T.; Tang, B. Organometallics 2000, 19, 2084-2089.
25. (i) Katayama, H.; Urushima, H.; Ozawa, F. J. Organomet. Chem. 2000, 606, 16-25.
26. (j) Saoud, M.; Romerosa, A.; Peruzzini, M. Organometallics 2000, 19, 4005-4007.
27. (k) van der Schaaf, P. A.; Kolly, R.; Kirner, H.-J.; Rime, F.; Mühlebach, A.; Hafner, A. J. Organomet. Chem. 2000, 606, 65-74.
28. (l) Hansen, S. M.; Volland, M. A. O.; Rominger, F.; Eisenträger, F.; Hofmann, P. Angew. Chem., Int. Ed. 1999, 38, 1273-1276.
29. (m) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799.
30. (n) Katayama, H.; Yoshida, T.; Ozawa, F. J. Organomet. Chem. 1998, 562, 203-206.
31. (a) Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 4035-4037.
32. (b) Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 2403-2405.
33. (c) Sanford, M. S.; Love, J. A.; Grubbs, R. H. Organometallics 2001, 20, 5314-5318.
34. (d) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225-3228.
35. (e) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.-Eur. J. 2001, 7, 3236-3253.
36. (f) Fürstner, A.; Krause, H.; Ackermann, L.; Lehmann, C. W. Chem. Commun. 2001, 2240-2241.
37. (g) Jafarpour, L.; Nolan, S. P. J. Organomet. Chem. 2001, 617-618, 17-27.
38. (h) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
39. (i) Katayama, H.; Urushima, H.; Nishioka, T.; Wada, C.; Nagao, M.; Ozawa, F. Angew. Chem., Int. Ed. 2000, 39, 4513-4515.
40. (j) Jafarpour, L.; Stevens, E. D.; Nolan, S. P. J. Organomet. Chem. 2000, 606, 49-54.
41. (k) Weskamp, T.; Kohl, F. J.; Hieringer, W.; Gleich, D.; Herrmann, W. A. Angew. Chem., Int. Ed. 1999, 38, 2416-2419.
42. (l) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
43. (m) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362-365.
44. (n) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
45. (o) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250.
46. (p) Schanz, H.-J.; Jafarpour, L.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5187-5190.
47. (q) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 1998, 37, 2490-2493; Angew. Chem., Int. Ed. 1999, 38, 262.
48. (q) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 1998, 37, 2490-2493; Angew. Chem., Int. Ed. 1999, 38, 262.
49. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
50. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
51. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
52. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
53. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
54. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
55. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
56. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
57. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
58. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
59. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
60. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
61. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
62. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
63. Recent reviews of olefin metathesis applications: (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (b) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043. (d) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000; Chapter 8. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077. (f) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. (g) Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565-588. (h) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (i) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. (k) Grubbs, R. H.; Khosravi, E.; Davidson, T. A.; Wagener, K. B. In Synthesis of Polymers: A Volume of the Materials Science and Technology Series; Schlüter, A.-D., Cahn, R. W., Haasen, P., Kramer, E. J., Eds.; Wiley-VCH: Weinheim, 1999; Chapter 3, pp 65-104 and Chapter 4, pp 105-122. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (l) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. (m) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240. (n) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555.
64. (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
65. (b) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181-222.
66. (c) Herrmann, W. A.; Weskamp, T.; Böhm, V. P. Adv. Organomet. Chem. 2001, 48, 1-69.
67. (d) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. 1998, 36, 22163-2187.
68. (a) Jackstell, R.; Andreau, M. G.; Frisch, A.; Selvakumar, K.; Zapf, A.; Klein, H.; Spannenberg, A.; Röttger, D.; Briel, O.; Karch, R.; Beller, M. Angew. Chem., Int. Ed. 2002, 41, 986-989.
69. (b) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 3202-3203.
70. (c) Albrecht, M.; Crabtree, R. H.; Mata, J.; Peris, E. Chem. Commun. 2002, 32-33.
71. (d) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411-1414.
72. (e) Peris, E.; Loch, J. A.; Mata, J.; Crabtree, R. H. Chem. Commun. 2001, 201-202.
73. (f) Mathews, C. J.; Smith, P. J.; Welton, T.; White, A. J. P.; Williams, D. J. Organometallics 2001, 20, 3848-3850.
74. (g) Powell, M. T.; Hou, D.-R.; Perry, M. C.; Cui, X.; Burgess, K. J. Am. Chem. Soc. 2001, 123, 8878-8879.
75. (h) Tulloch, A. D.; Danopoulos, A. A.; Tooze, R. P.; Cafferkey, S. M.; Kleinhenz, S.; Hursthouse, M. B. Chem. Commun. 2000, 1247-1248.
76. (i) McGuinness, D. S.; Cavell, K. J. Organometallics 2000, 19, 741-748.
77. (j) Chen, J. C. C.; Lin, I. J. B. Organometallics 2000, 19, 5113-5121.
78. (k) Gardiner, M. G.; Herrmann, W. A.; Reisinger, C.-P.; Schwarz, J.; Spiegler, M. J. Organomet. Chem. 1999, 572, 239-247.
79. (l) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 1999, 585, 348-352.
80. (m) McGuinness, D. S.; Green, M. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1998, 565, 165-178.
81. (n) Lappert, M. F.; Maskell, R. K. J. Organomet. Chem. 1984, 264, 217-228.
82. (o) Hill, J. E.; Nile, T. A. Transition Met. Chem. 1978, 3, 315-316.
83. Other methods include the reduction of thiones, nucleophilic addition to coordinated isocyanide ligands, and carbene transfer from one metal center to another. Reviews: (a) Raubenheimer, H. G.; Cronje, S. J. Organomet. Chem. 2001, 617-618, 170-181. (b) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 2000, 600, 12-22. (c) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91. (d) Liu, S.-T.; Reddy, K. R. Chem. Soc. Rev. 1999, 28, 315-322.
84. Other methods include the reduction of thiones, nucleophilic addition to coordinated isocyanide ligands, and carbene transfer from one metal center to another. Reviews: (a) Raubenheimer, H. G.; Cronje, S. J. Organomet. Chem. 2001, 617-618, 170-181. (b) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 2000, 600, 12-22. (c) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91. (d) Liu, S.-T.; Reddy, K. R. Chem. Soc. Rev. 1999, 28, 315-322.
85. Other methods include the reduction of thiones, nucleophilic addition to coordinated isocyanide ligands, and carbene transfer from one metal center to another. Reviews: (a) Raubenheimer, H. G.; Cronje, S. J. Organomet. Chem. 2001, 617-618, 170-181. (b) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 2000, 600, 12-22. (c) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91. (d) Liu, S.-T.; Reddy, K. R. Chem. Soc. Rev. 1999, 28, 315-322.
86. Other methods include the reduction of thiones, nucleophilic addition to coordinated isocyanide ligands, and carbene transfer from one metal center to another. Reviews: (a) Raubenheimer, H. G.; Cronje, S. J. Organomet. Chem. 2001, 617-618, 170-181. (b) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 2000, 600, 12-22. (c) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91. (d) Liu, S.-T.; Reddy, K. R. Chem. Soc. Rev. 1999, 28, 315-322.
87. (a) Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-214.
88. (b) Hitchcock, P. B.; Lappert, M. F.; Pye, P. L. J. Chem. Soc., Dalton Trans. 1978, 826-836.
89. (c) Lappert, M. F.; Pye, P. L. J. Chem. Soc., Dalton Trans. 1978, 837-844.
90. (d) Lappert, M. F.; Pye, P. L. J. Chem. Soc., Dalton Trans. 1977, 2172-2180.
91. (e) Lappert, M. F. J. Organomet. Chem. 1975, 100, 139-159.
92. (f) Çetinkaya, B.; Dixneuf, P.; Lappert, M. F. J. Chem. Soc., Dalton Trans. 1974, 1827-1833.
93. (a) Arduengo, A. J.; Davidson, F.; Dias, H. V. R.; Goerlich, J. R.; Khasnis, D.; Marshall, W. J.; Prakasha, T. K. J. Am. Chem. Soc. 1997, 119, 12742-12749.
94. (b) Arduengo, A. J.; Goerlich, J. R.; Marshall, W. J. J. Am. Chem. Soc. 1995, 117, 11027-11028.
95. (c) Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
96. The mechanism of this process has not been studied, but we believe that some free carbene is released from the adduct in solution. Coordination of the free NHC to the metal center would then drive the adduct-carbene equilibrium toward more free carbene. This mechanism is supported by the observation that free carbenes are obtained when the adducts are heated under vacuum to remove the alcohol or chloroform byproduct (ref 17). However, a metal-facilitated adduct deprotection or ligand substitution mechanism cannot be discounted at this time.
97. (a) Cardin, D. J.; Çetinkaya, B.; Çetinkaya, E.; Lappert, M. F. J. Chem. Soc., Dalton Trans. 1973, 514-522.
98. (b) Chamizo, J. A.; Lappert, M. F. In Advances in Metal Carbene Chemistry; Schubert, U., Ed.; Kluwer Academic Publishers: Norwell, MA. 1989; pp 47-58.
99. (a) Çetinkaya, B.; Çetinkaya, B.; E.; Chamizo, J. A.; Hitchcock, P. B.; Jasim, H. A.; Küçükbay, H.; Lappert, M. F. J. Chem. Soc., Perkin Trans. 1 1998, 2047-2054.
100. (b) Çetinkaya, E.; Hitchcock, P. B.; Jasim, H. A.; Lappert, M. F.; Kostas, S. J. Chem. Soc., Perkin Trans. 1 1992, 561-567.
101. (c) Wanzlick, H. W. Angew. Chem., Int. Ed. Engl. 1962, 1, 75-80.
102. Hitchcock, P. B. J. Chem. Soc., Dalton Trans. 1979, 1314-1317.
103. (a) Moss, R. A. Acc. Chem. Res. 1999, 32, 969-974.
104. (b) Ross, J. P.; Couture, P.; Warkentin, J. Can. J. Chem. 1997, 75, 1331-1335.
105. (c) Couture, P.; Warkentin, J. Can. J. Chem. 1997, 75, 1281-1294.
106. (d) Couture, P.; Terlouw, J. K.; Warkentin, J. J. Am. Chem. Soc. 1996, 118, 4214-4215.
107. (e) Rigby, J. H.; Cavezza, A.; Ahmed, G. J. Am. Chem. Soc. 1996, 118, 12848-12849.
108. (a) Lappert, M. F.; Pye, P. L. J. Less-Common Met. 1997, 54, 191-207.
109. (b) Hocker, J.; Merten, R. Angew. Chem., Int. Ed. Engl. 1972, 11, 964-973.
110. (c) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1968, 7, 754-765.
111. (d) Wiberg, N. Angew. Chem., Int. Ed. Engl. 1968, 7, 766-779.
112. (a) Teles, J. H.; Melder, J.-P.; Ebel, K.; Schneider, R.; Gehrer, E.; Harder, W.; Brode, S.; Enders, D.; Breuer, K.; Raabe, G. Helv. Chim. Acta 1996, 79, 61-83.
113. (b) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021-1023.
114. For preliminary results, see: Grubbs, R. H.; Trnka, T. M. U.S. Patent 6,-426, 419 B1, 2002.
115. 3 Tri carbene also has been reported by Fürstner and co-workers. See ref 4e.
116. 2Ru=CHR system.
117. For preliminary results, see ref4n and Grubbs, R. H.; Scholl, M. PCT Int. Appl. WO 0071554, 2000.
118. Arduengo, A. J.; Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich, J. R.; Marshall, W. J.; Unverzagt, M. Tetrahedron 1999, 55, 14523-14534.
119. Arduengo, A. J.; Dias, H. V. R.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530-5534.
120. Morgan, J. P.; Goldberg, S. D.; Grubbs, R. H. 2001, unpublished results.
121. (a) Gill, D. F.; Shaw, B. L. Inorg. Chim. Acta 1979, 32, 19-23.
122. (b) Esteruelas, M. A.; Werner, H. J. Organomet. Chem. 1986, 303, 221-231.
123. (c) Moers, F. G.; Langhout, J. P. Recueil 1972, 91, 591-600.
124. (d) James, B. R.; Preece, M.; Robinson, S. D. In Catalytic Aspects of Metal Phosphine Complexes; Alyea, E. C., Meek, D. W., Eds.; American Chemical Society: Washington, DC, 1982; pp 145-161.
125. 2Ru=CH(OEt). Louie, J.; Grubbs, R. H. Organometallics 2002, 21, 2153-2164.
126. 6) as well. Coalter, J. N.; Caulton, K. G. New J. Chem. 2001, 25, 679-684.
127. 2(Cl)(CO)Ir, Churchill, M. R.; Fettinger, J. C.; Buttrey, L. A.; Barkan, M. D.; Thompson, J. S. J. Organomet. Chem. 1988, 340, 257-266.
128. 2(Cl)(CO)Ir, Churchill, M. R.; Fettinger, J. C.; Buttrey, L. A.; Barkan, M. D.; Thompson, J. S. J. Organomet. Chem. 1988, 340, 257-266.
129. 2(Cl)(CO)Ir, Churchill, M. R.; Fettinger, J. C.; Buttrey, L. A.; Barkan, M. D.; Thompson, J. S. J. Organomet. Chem. 1988, 340, 257-266.
130. 2(Cl)(CO)Ir, Churchill, M. R.; Fettinger, J. C.; Buttrey, L. A.; Barkan, M. D.; Thompson, J. S. J. Organomet. Chem. 1988, 340, 257-266.
131. This test is part of the International Union of Crystallography CIF checking program. Hirshfeld, F. L. Acta Crystallogr. 1976, A32, 239-244.
132. Jafarpour, L.; Nolan, S. P. Organometallics 2000, 19, 2055-2057.
133. Jafarpour, L.; Hillier, A. C.; Nolan, S. P. Organometallics 2002, 21, 442-444.
134. Huang, J.; Stevens, E. D.; Nolan, S. P. Organometallics 2000, 19, 1194-1197.
135. Jazzar, R. F. R.; Macgregor, S. A.; Mahon, M. F.; Richards, S. P.; Whittlesey, M. K. J. Am. Chem. Soc. 2002, 124, 4944-4945.
136. 2Ru=CH(OEt), ref 26a.
137. 2Ru=CH(OEt), ref 26a.
138. 2Ru=CH(OEt), ref 26a.
139. 2Ru=CH(OEt), ref 26a.
140. 2(Cl)-(CO)(H)Ru, Werner, H.; Stüer, W.; Weberndörfer, B.; Wolf, J. Eur. J. Inorg. Chem. 1999, 1707-1713.
141. 2(Cl)-(CO)(H)Ru, Werner, H.; Stüer, W.; Weberndörfer, B.; Wolf, J. Eur. J. Inorg. Chem. 1999, 1707-1713.
142. 2(Cl)-(CO)(H)Ru, Werner, H.; Stüer, W.; Weberndörfer, B.; Wolf, J. Eur. J. Inorg. Chem. 1999, 1707-1713.
143. 2(Cl)-(CO)(H)Ru, Werner, H.; Stüer, W.; Weberndörfer, B.; Wolf, J. Eur. J. Inorg. Chem. 1999, 1707-1713.
144. 3)(IMes)(Cl)(CO)Ru, Lee, H. M.; Smith, D. C.; He, Z.; Stevens, E. D.; Yi, C. S.; Nolan, S. P. Organometallics 2001, 20, 794-797.
145. 2(Cl)(CO)(H)Ru, ref 25c and d.
146. 2- (Cl)(CO)(Ph)Ru, ref 34c.
147. 2(Cl)-(CO)(H)Ru, ref 34b.
148. 2(Cl)(CO)(H)Ru, Esteruelas, M. A.; Werner, H. J. Organomet. Chem. 1986, 303, 221-231.
149. This geometry was confirmed in the crystal structure of 5. Sanford, M. S. Ph.D. Thesis, California Institute of Technology, Pasadena, CA, 2001.
150. Yi, C. S.; Lee, D. W.; Chen, Y. Organometallics 1999, 18, 2043-2045.
151. Esteruelas, M. A.; Lahoz, F. J.; Oñate, E.; Oro, L. A.; Zeier, B. Organometallics 1994, 13, 4258-4265.
152. Harlow, K. J.; Hill, A. F.; Welton, T. J. Chem. Soc., Dalton Trans. 1999, 1911-1912.
153. Arduengo, A. J.; Calabrese, J. C.; Davidson, F.; Dias, H. V. R.; Goerlich, J. R.; Krafczyk, R.; Marshall, W. J.; Tamm, M.; Schmutzler, R. Helv. Chim. Acta 1999, 82, 2348-2364.
154. (a) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749-750.
155. (b) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543-6554.
156. Other ruthenium alkylidene complexes (including 2) also can be purified in this way. (a) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799. (b) Tallarico, J. A.; Bonitatebus, P. J.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157-7158.
157. Other ruthenium alkylidene complexes (including 2) also can be purified in this way. (a) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799. (b) Tallarico, J. A.; Bonitatebus, P. J.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157-7158.
158. Love, J. A.; Sanford, M. S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, in press.
159. Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Chem. Soc. 1999, 121, 2674-2678.
160. Mol, J. C. Green Chem. 2002, 4, 5-13.
161. 1H NMR.
162. (a) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274-4277.
163. (b) Bielawski, C. W.; Grubbs, R. H. Angew. Chem., Int. Ed. 2000, 39, 2903-2906.
164. Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153-3155.
165. (a) Simms, R. W.; Drewitt, M. J.; Baird, M. C. Organometallics 2002, 21, 2958-2963.
166. (b) Titcomb, L. R.; Caddick, S.; Cloke, F. G. N.; Wilson, D. J.; McKerrecher, D. Chem. Commun. 2001, 1388-1389.
167. Denk, K.; Sirsch, P.; Herrmann, W. A. J. Organomet. Chem. 2002, 649, 219-224.
168. Schürer, S. C.; Gessler, S.; Buschmann, N.; Blechert, S. Angew. Chem., Int. Ed. 2000, 39, 3898-3901.
169. Trnka, T. M.; Grubbs, R. H. 1999, unpublished work.
170. (a) Wolsey, W. C. J. Chem. Educ. 1973, 50, A335-A337.
171. (b) Muse, L. A. J. Chem. Educ. 1972, 49, A463-A466.
172. (c) Everett, K.; Graf, F. A. In CRC Handbook of Laboratory Safety, 2nd ed.; Steere, N. V., Ed.; CRC Press: Boca Raton, FL, 1971; pp 265-276.
173. Kirkland, T. A.; Grubbs, R. H. J. Org. Chem. 1997, 62, 7310-7318.
174. Moers, F. G.; Ten Hoedt, R. W. M.; Langhout, J. P. J. Inorg. Nucl. Chem. 1974, 36, 2279-2282.
175. VNMR 6.1B Software; Varian Associates, Inc.
176. (a) Bruker 1999 SMART, SAINT, and SHELXTL. Bruker AXS Inc., Madison. WI.
177. (b) Diamond 2.1. 2000 Crystal Impact GbR, Bonn, Germany.