Multicatalytic processes using diverse transition metals for the synthesis of alkenes

Journal of the American Chemical Society

Volumn 126, Issue 36, 2004, Pages 11152-11153

  Lebel, Hélène ^a   Paquet, Vaĺrie ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; OLEFINATION; RING CLOSING METATHESIS; SYNTHESIS;

EID: 4544268240     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0472681     Document Type: Article

References (47)

1. For recent reviews: (a) Soderberg, B. C. G. Coord. Chem. Rev. 2003, 241, 147-247.
2. (b) Haughton, L.; Williams, J. M. J. J. Chem. Soc., Perkin Trans, 1 2000, 3335-3349.
3. Bruggink, A.; Schoevaart, R.; Kieboom, T. Org. Process Res. Dev. 2003, 7, 622-640.
4. (a) Ostaszewski, R.; Portlock, D. E.; Fryszkowska, A.; Jeziorska, K. Pure Appl. Chem. 2003, 75, 413-419.
5. (b) Schoemaker, H. E.; Mink, D.; Wubbolts, M. G. Science 2003, 299, 1694-1698.
6. (c) Kodier, K. M.; Wong, C. H. Nature 2001, 409, 232-240.
7. (d) Carrea, G.; Riva, S. Angew. Chem., Int. Ed. 2000, 39, 2226-2254.
8. (e) Koeller, K. M.; Wong, C. H. Chem. Rev. 2000, 100, 4465-4493.
9. Recent reviews: (a) Pamies, O.; Backvall, J. E. Chem. Rev. 2003, 103, 3247-3261.
10. Selected examples: (b) Persson, B. A.; Larsson, A. L. E.; Le Ray, M.; Backvall, J. E. J. Am. Chem. Soc. 1999, 121, 1645-1650.
11. (c) Larsson, A. L. E.; Persson, B. A.; Backvall, J. E. Angew. Chem., Int. Ed. 1997, 36, 1211-1212.
12. (d) Reetz, M. T.; Schimossek, K. Chimia 1996, 50, 668-669.
13. (e) Dinh, P. M.; Howarth, J. A.; Hudnott, A. R.; Williams, J. M. J.; Harris, W. Tetrahedron Lett. 1996, 37, 7623-7626.
14. Review: (a) Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33, 302-312.
15. A few examples have recently appeared in the litterature: (b) Siebeneicher, H.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 2003, 42, 3042-3044.
16. (c) Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Milton, M. D.; Hidai, M.; Uemura, S. Angew. Chem., Int. Ed. 2003, 42, 2681-2684.
17. (d) Cossy, J.; Bargiggia, F.; BouzBouz, S. Org. Lett. 2003, 5, 459-462.
18. (e) Ko, S.; Lee, C.; Choi, M. G.; Na, Y.; Chang, S. J. Org. Chem. 2002, 68, 1607-1610.
19. Processes in which the first intermediate is spontaneously converted to another product: (a) Catellani, M. Synlett 2003, 298-313.
20. (b) McCarroll, A. J.; Wallon, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215-3229.
21. (c) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195-206.
22. (d) Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
23. Selected references: (a) Bressette, A. R.; Glover, L. C. Synlett 2004, 738-740.
24. (b) Reid, M.; Rowe, D. J.; Taylor, R. J. K. Chem. Commun. 2003. 2284-2285.
25. (c) Blackburn, L.; Kanno, H.; Taylor, R. J. K. Tetrahedron Lett. 2003, 44, 115-118.
26. (d) MacCoss, R. N.; Balskus, E. P.; Ley, S. V. Tetrahedron Lett. 2003, 44, 7779-7781. See Supporting Information for other ref.
27. Jensen, D. R.; Schultz, M. J.; Mueller, J. A.; Sigman, M. S. Angew. Chem., Int. Ed. 2003, 42, 3810-3813.
28. (a) Lebel, H.; Paquet, V. J. Am. Chem. Soc. 2004, 126, 320-328.
29. (b) Lebel, H.; Paquet, V. Organometallics 2004, 23, 1187-1190.
30. (c) Lebel, H.; Paquet, V. Org. Lett. 2002, 4, 1671-1674.
31. (d) Grasa, G. A.; Moore, Z.; Martin, K. L.; Stevens, E. D.; Nolan, S. P.; Paquet, V.; Lebel, H. J. Organomet. Chem. 2002, 658, 126-131.
32. (e) Lebel, H.; Paquet, V.; Proulx, C. Angew. Chem., Int. Ed. 2001, 40, 2887-2890.
33. Methylenation of ketones: Lebel, H.; Guay, D.; Paquet, V.; Huard, K. Org. Lett. 2004, 6, 3047-3050.
34. See Supporting Information for the structure of catalyst 1 (ref 8).
35. (a) Grubbs, R. H. Adv. Synth. Catal. 2002, 344, 569-569.
36. (b) Furstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236-3253.
37. Stoichiometric olefination-metathesis processes are known with the Tebbe reagent: (a) Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 855-856.
38. (b) Stille, J. R.; Santarsiero, B. D.; Grubbs, R. H. J. Org. Chem. 1990, 55, 843-862.
39. (c) Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335-10336.
40. (a) Trnka, T. M.; Morgan, J. P.; Sanford, M. S.; Wilhelm, T. E.; Scholl, M.; Choi, T. L.; Ding, S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 2546-2558.
41. (b) Love, J. A.; Sanford, M. S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 10103-10109.
42. (c) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001. 123, 749-750.
43. (d) Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000. 2, 3153-3155.
44. Yoakim, C.; Guse, I.; O'Meara, J. A.; Thavonekham, B. Synlett 2003, 473-476. See Supporting Information for the structure of the DPPBE phosphine 17.
45. (a) Jafarpour, L.; Hillier, A. C.; Nolan, S. P. Organometallics 2002, 21, 442-444. See Supporting Info for the structure of catalyst 16.
46. Chang, S. B.; Grubbs, R. H. J. Org. Chem. 1998, 63, 864-866.
47. Kahnberg, P.; Lee, C. W.; Grubbs, R. H.; Sterner, O. Tetrahedron 2002, 55, 5203-5208.