An air-stable, reusable, bimetallic version of Grubbs' catalyst for alkene metathesis

Synlett

Volumn , Issue 11, 2002, Pages 1925-1927

  Maishal, Tarun K ^a   Sarkar, Amitabha ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Carbene complexes; Catalysis; Metathesis; Organometallic reagents; Ruthenium

Indexed keywords

ALKENE; ORGANOMETALLIC COMPOUND; REAGENT; RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; REACTION ANALYSIS; RING CLOSING METATHESIS;

EID: 0036423026     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34867     Document Type: Article

References (24)

1. Current address: Department of Organic Chemistry, Indian Association for the Cultivation of Science, Kolkata - 700 032, India. E-mail: ocas@mahendra.iacs.res.in.
2. (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
3. (b) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
4. (c) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
5. (d) Schuster, M.; Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036.
6. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
7. (f) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
8. (a) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543.
9. (b) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887.
10. Recycling catalyst: (a) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J. Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791. (b) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (c) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.-Eur. J. 2001, 7, 3236. (d) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657.(e) For a survey of Rubased initiators with other alkylidene groups, see: Frenzel, U.; Nuyken, O. J. Polym. Sci. A 2002, 40, 2895.
11. Recycling catalyst: (a) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J. Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791. (b) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (c) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.-Eur. J. 2001, 7, 3236. (d) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657.(e) For a survey of Rubased initiators with other alkylidene groups, see: Frenzel, U.; Nuyken, O. J. Polym. Sci. A 2002, 40, 2895.
12. Recycling catalyst: (a) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J. Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791. (b) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (c) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.-Eur. J. 2001, 7, 3236. (d) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657.(e) For a survey of Rubased initiators with other alkylidene groups, see: Frenzel, U.; Nuyken, O. J. Polym. Sci. A 2002, 40, 2895.
13. Recycling catalyst: (a) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J. Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791. (b) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (c) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.-Eur. J. 2001, 7, 3236. (d) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657.(e) For a survey of Rubased initiators with other alkylidene groups, see: Frenzel, U.; Nuyken, O. J. Polym. Sci. A 2002, 40, 2895.
14. Recycling catalyst: (a) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J. Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791. (b) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (c) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.-Eur. J. 2001, 7, 3236. (d) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657.(e) For a survey of Rubased initiators with other alkylidene groups, see: Frenzel, U.; Nuyken, O. J. Polym. Sci. A 2002, 40, 2895.
15. We have followed the procedures described in (a) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100. (b) Trnka, T. M.; Day, M. W.; Grubbs, R. H. Angew. Chem. Int. Ed. 2001, 40, 3441.
16. We have followed the procedures described in (a) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100. (b) Trnka, T. M.; Day, M. W.; Grubbs, R. H. Angew. Chem. Int. Ed. 2001, 40, 3441.
17. 3). Details of preparation and complete characterization including crystal structure will be reported separately.
18. 13C NMR spectra, and satisfactory elemental analyses were obtained for all new compounds.
19. For examples of RCM on organometallic substrates, see: (a) Sültemeyer, J.; Dötz, K. H.; Hupfer, H.; Nieger, M. J. Orgmet. Chem. 2000, 606, 26. (b) Zhang, L.; Herndon, J. W. Tetrahedron Lett. 2002, 43, 4471. (c) Licandro, E.; Maiorana, S.; Vandoni, B.; Perdicchia, D.; Paravidino, P.; Baldoli, C. Synlett 2001, 757. (d) Maity, B. C.; Swamy, V. M.; Sarkar, A. Tetrahedron Lett. 2001, 42, 4373.
20. For examples of RCM on organometallic substrates, see: (a) Sültemeyer, J.; Dötz, K. H.; Hupfer, H.; Nieger, M. J. Orgmet. Chem. 2000, 606, 26. (b) Zhang, L.; Herndon, J. W. Tetrahedron Lett. 2002, 43, 4471. (c) Licandro, E.; Maiorana, S.; Vandoni, B.; Perdicchia, D.; Paravidino, P.; Baldoli, C. Synlett 2001, 757. (d) Maity, B. C.; Swamy, V. M.; Sarkar, A. Tetrahedron Lett. 2001, 42, 4373.
21. For examples of RCM on organometallic substrates, see: (a) Sültemeyer, J.; Dötz, K. H.; Hupfer, H.; Nieger, M. J. Orgmet. Chem. 2000, 606, 26. (b) Zhang, L.; Herndon, J. W. Tetrahedron Lett. 2002, 43, 4471. (c) Licandro, E.; Maiorana, S.; Vandoni, B.; Perdicchia, D.; Paravidino, P.; Baldoli, C. Synlett 2001, 757. (d) Maity, B. C.; Swamy, V. M.; Sarkar, A. Tetrahedron Lett. 2001, 42, 4373.
22. For examples of RCM on organometallic substrates, see: (a) Sültemeyer, J.; Dötz, K. H.; Hupfer, H.; Nieger, M. J. Orgmet. Chem. 2000, 606, 26. (b) Zhang, L.; Herndon, J. W. Tetrahedron Lett. 2002, 43, 4471. (c) Licandro, E.; Maiorana, S.; Vandoni, B.; Perdicchia, D.; Paravidino, P.; Baldoli, C. Synlett 2001, 757. (d) Maity, B. C.; Swamy, V. M.; Sarkar, A. Tetrahedron Lett. 2001, 42, 4373.
23. 2 complex, IV, does not readily react with vinylferrocene at room temperature. However, on heating under reflux in dichloromethane with 1.2-1.5 equivalent of vinylferrocene, complex IV affords >80% yield of complex III.
24. Maishal, T. K.; Sinha-Mahapatra, D. K.; Paranjape, K.; Sarkar, A. Tetrahedron Lett. 2002, 43, 2263.