A stable ruthenium catalyst for productive olefin metathesis

Organometallics

Volumn 23, Issue 21, 2004, Pages 4824-4827

  Forman, Grant S ^a   McConnell, Ann E ^a   Hanton, Martin J ^a   Slawin, Alexandra M Z ^b   Tooze, Robert P ^a   Van Rensburg, Werner Janse ^a   Meyer, Wolfgang H ^a   Dwyer, Cathy ^a   Kirk, Megan M ^a   Wynand Serfontein, D ^a  

^a SASOL TECHNOLOGY PTY LTD   (South Africa)

^b UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; HIGH TEMPERATURE EFFECTS; ISOMERS; OLEFINS; RUTHENIUM; SUBSTITUTION REACTIONS; X RAY DIFFRACTION;

CARBENES; CROSS METATHESIS (CM); METATHESIS; MOIETY;

ORGANOMETALLICS;

EID: 6344253335     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049370c     Document Type: Article

References (89)

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6. For recent reviews on olefin metathesis, see: (a) Schuster, M.; Blechart, S. Angew Chem., Int. Ed. 1997, 109, 2037-2056. (b) Fürstner, A. Top. Catal. 1997, 4, 285-299. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (e) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75-89. (f) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555. (g) Fürstner, A. Angew Chem., Int. Ed. 2000, 39, 3012-3043. (h) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (k) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2078-2077. Coates, G. W. Dalton 2002, 467-475. (n) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (o) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
7. For recent reviews on olefin metathesis, see: (a) Schuster, M.; Blechart, S. Angew Chem., Int. Ed. 1997, 109, 2037-2056. (b) Fürstner, A. Top. Catal. 1997, 4, 285-299. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (e) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75-89. (f) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555. (g) Fürstner, A. Angew Chem., Int. Ed. 2000, 39, 3012-3043. (h) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (k) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2078-2077. Coates, G. W. Dalton 2002, 467-475. (n) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (o) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
8. For recent reviews on olefin metathesis, see: (a) Schuster, M.; Blechart, S. Angew Chem., Int. Ed. 1997, 109, 2037-2056. (b) Fürstner, A. Top. Catal. 1997, 4, 285-299. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. (e) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75-89. (f) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555. (g) Fürstner, A. Angew Chem., Int. Ed. 2000, 39, 3012-3043. (h) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565-1604. Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885. (j) Yet, L. Chem. Rev. 2000, 100, 2963-3007. (k) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529. Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2078-2077. Coates, G. W. Dalton 2002, 467-475. (n) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561. (o) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
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33. For selected examples, see: (a) Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751-1753. (b) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784. Choi, T.-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417-10418. Chatterjee, A. K.; Choi, T. L.; Grubbs, R. H. Synlett 2001, 1034-1037. (e) Choi, T. L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 1277-1279. (f) Grela, K. Bieniek, M. Tetrahedron Lett. 2001, 42, 6425-6428. (g) Morgan, J. P.; Morrill, C.; Grubbs, R. H. Org. Lett. 2002, 4, 67-73. (h) Chatterjee, A. K.; Sanders, D. P.; Grubbs, R. H. Org. Lett. 2002, 4, 1939-1942. Van Nguyen, T.; Debenedetti, S.; De Kimpe, N. Tetrahedron Lett. 2003, 44, 4199-4201.
34. For selected examples, see: (a) Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751-1753. (b) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784. Choi, T.-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417-10418. Chatterjee, A. K.; Choi, T. L.; Grubbs, R. H. Synlett 2001, 1034-1037. (e) Choi, T. L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 1277-1279. (f) Grela, K. Bieniek, M. Tetrahedron Lett. 2001, 42, 6425-6428. (g) Morgan, J. P.; Morrill, C.; Grubbs, R. H. Org. Lett. 2002, 4, 67-73. (h) Chatterjee, A. K.; Sanders, D. P.; Grubbs, R. H. Org. Lett. 2002, 4, 1939-1942. Van Nguyen, T.; Debenedetti, S.; De Kimpe, N. Tetrahedron Lett. 2003, 44, 4199-4201.
35. For selected examples, see: (a) Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751-1753. (b) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784. Choi, T.-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417-10418. Chatterjee, A. K.; Choi, T. L.; Grubbs, R. H. Synlett 2001, 1034-1037. (e) Choi, T. L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 1277-1279. (f) Grela, K. Bieniek, M. Tetrahedron Lett. 2001, 42, 6425-6428. (g) Morgan, J. P.; Morrill, C.; Grubbs, R. H. Org. Lett. 2002, 4, 67-73. (h) Chatterjee, A. K.; Sanders, D. P.; Grubbs, R. H. Org. Lett. 2002, 4, 1939-1942. Van Nguyen, T.; Debenedetti, S.; De Kimpe, N. Tetrahedron Lett. 2003, 44, 4199-4201.
36. For selected examples, see: (a) Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751-1753. (b) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784. Choi, T.-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417-10418. Chatterjee, A. K.; Choi, T. L.; Grubbs, R. H. Synlett 2001, 1034-1037. (e) Choi, T. L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 1277-1279. (f) Grela, K. Bieniek, M. Tetrahedron Lett. 2001, 42, 6425-6428. (g) Morgan, J. P.; Morrill, C.; Grubbs, R. H. Org. Lett. 2002, 4, 67-73. (h) Chatterjee, A. K.; Sanders, D. P.; Grubbs, R. H. Org. Lett. 2002, 4, 1939-1942. Van Nguyen, T.; Debenedetti, S.; De Kimpe, N. Tetrahedron Lett. 2003, 44, 4199-4201.
37. For selected examples, see: (a) Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751-1753. (b) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784. Choi, T.-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417-10418. Chatterjee, A. K.; Choi, T. L.; Grubbs, R. H. Synlett 2001, 1034-1037. (e) Choi, T. L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 1277-1279. (f) Grela, K. Bieniek, M. Tetrahedron Lett. 2001, 42, 6425-6428. (g) Morgan, J. P.; Morrill, C.; Grubbs, R. H. Org. Lett. 2002, 4, 67-73. (h) Chatterjee, A. K.; Sanders, D. P.; Grubbs, R. H. Org. Lett. 2002, 4, 1939-1942. Van Nguyen, T.; Debenedetti, S.; De Kimpe, N. Tetrahedron Lett. 2003, 44, 4199-4201.
38. For selected examples, see: (a) Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751-1753. (b) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784. Choi, T.-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417-10418. Chatterjee, A. K.; Choi, T. L.; Grubbs, R. H. Synlett 2001, 1034-1037. (e) Choi, T. L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 1277-1279. (f) Grela, K. Bieniek, M. Tetrahedron Lett. 2001, 42, 6425-6428. (g) Morgan, J. P.; Morrill, C.; Grubbs, R. H. Org. Lett. 2002, 4, 67-73. (h) Chatterjee, A. K.; Sanders, D. P.; Grubbs, R. H. Org. Lett. 2002, 4, 1939-1942. Van Nguyen, T.; Debenedetti, S.; De Kimpe, N. Tetrahedron Lett. 2003, 44, 4199-4201.
39. For selected examples, see: (a) Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751-1753. (b) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784. Choi, T.-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417-10418. Chatterjee, A. K.; Choi, T. L.; Grubbs, R. H. Synlett 2001, 1034-1037. (e) Choi, T. L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 1277-1279. (f) Grela, K. Bieniek, M. Tetrahedron Lett. 2001, 42, 6425-6428. (g) Morgan, J. P.; Morrill, C.; Grubbs, R. H. Org. Lett. 2002, 4, 67-73. (h) Chatterjee, A. K.; Sanders, D. P.; Grubbs, R. H. Org. Lett. 2002, 4, 1939-1942. Van Nguyen, T.; Debenedetti, S.; De Kimpe, N. Tetrahedron Lett. 2003, 44, 4199-4201.
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74. 12
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77. 8) analysis of the reaction mixture indicated quantitative conversion of 4 to 5. The reduced yield is largely due to the partial solubility of 5 in hexanes mixtures.
78. When isomerically pure 3b was reacted with 4, no identifiable products were recovered.
79. Full details of these studies will be disclosed in due course.
80. Extensive NMR studies indicate that 6 is resolved into a number of rotational isomers at low temperature. Full details of these studies will be disclosed in due course.
81. int = 0.1270), R1 = 0.0520, wR2 = 0.0549, Flack parameter 0.01(4). The file CCDC-239497 contains supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB21EZ, U.K.; fax, (+44) 1223-336-033; e-mail, deposit@ccdc.cam.ac.uk).
82. When the identical decomposition reaction was performed at 70°C, no ethylene formation was observed.
83. 2 (10) decomposed with a half-life of 36 min at 70°C. See the Supporting Information for more details.
84. 5a
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88. See the Supporting Information for more details.
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