Ring-rearrangement metathesis (RRM) mediated by ruthenium-indenylidene complexes

European Journal of Organic Chemistry

Volumn , Issue 5, 2010, Pages 937-943

  Clavier, Hervé ^a,b   Broggi, Julie ^a   Nolan, Steven P ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

Carbene ligands; Metathesis; Nitrogen heterocycles; Phosphanes; Rearrangment; Ruthenium

Indexed keywords

EID: 76149101592     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901316     Document Type: Article

References (43)

1. For reviews on metathesis, see: a) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172;
2. Angew. Chem. Int. Ed. 2000. 39, 3013-3043;
3. b) T. M. Trnka, R. H. Grubbs, Acc: Chem. Res. 2001, 34, 18-29;
4. c) Handbook of Metathesis (Ed.: R. H. Grubbs), Wiley VCH, Weinheim, 2003, p. 1204;
5. d) P. H. Deshmukh, S. Blechert, Dalton Trans. 2007, 2479-2491;
6. e) C. Samojłwicz, M. Bieniek. K. Grela, Chem. Rev. 2009, 109, 3708-3742.
7. a) M. R. Buehmeiser, Chem. Rev. 2000, 100, 1565-1604;
8. b) C. Slugovc. Mucromol. Rapid Commun. 2004, 25, 1283-1297.
9. a) S. K. Chattopadhyay, S. Karmakar, T. Biswas, K. C. Majumdar. H. Rahaman, B. Roy. Tetrahedron 2007, 63. 3919-3952:
10. b) S. T. Diver, Coord. Chem. Rev. 2007, 251, 671-701;
11. c) M. Mori, Adv. Synth. Catal. 2007, 349, 121-135.
12. S. J. Connon, S. Blechert. Angew. Chem. 2003, 115. 1944-1968;
13. Angew. Chem. Int. Ed. 2003, 42, 1900-1923.
14. N. Holub, S. Blechert. Chem. Asian J. 2007, 2, 1064-1082.
15. For selected references, see: a) W. J. Zuercher, M. Hashimoto. R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640;
16. b) R. Stragies, S. Blechert, Synlett 1998, 169-171;
17. c) S. N. Osipov N. M. Robelikova, G. T. Shchetnikov, A. F. Kolomiets, C. Bruneau, R H. Dixneuf, Synlett 2001, 621-622;
18. d) L. C. Usher, M. Estrella-Jimenez, I. Ghiviriga. D. L. Wright. Angew. Chem. Int. Ed. 2002, 41, 4560-4562:
19. e) T. Kitamuru, Y. Kuzubu. Y. Sato. H. Wakamatsu. R. Fujita. M. Mori, Tetrahedron 2004, 60, 7375-7389:
20. f) J. Holtsclaw. M. koreeda, Org. Lett. 2004, 6, 3719-3722:
21. g) C. K. Malik, S. Ghosh, Org. Lett. 2007, 9, 2537-2540;
22. h) G. Barbe, A. B. Charette, J. Am. Chem. Soc. 2008, 130, 13873-13874;
23. i) J.A. Herderson, A.J. Phillips, Angew. Chem. Int. Ed. 2008, 47, 4899-4902.
24. a) J. Huang, H. J. Schanz, E. D. Stevens, S. P. Nolan, Organometallics 1999, 18, 2370- 2375;
25. b) A. Fürstner, O. R. Thiel, L. Ackermann, H. J. Schanz, S. P. Nolan, J. Org. Chem. 2000, 65, 2204- 2207;
26. c) H. Clavier. S. P. Nolan, Chem. Eur. J. 2007, 13, 8029- 8036;
27. d) F. Boeda, X. Bantreil, H. Clavier. S. P. Nolan, Adv. Synth. Catal 2008, 350, 2959- 2966;
28. e) H. Clavier, C. A. Urbina-Blanco, S. P. Nolan. Organometallics 2009, 28, 2848-2854;
29. f) For use of late transition-metal complexes bearing NHC ligands in catalysis, see: S. Diez-González, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612- 3676.
30. a) A. Fürstner, O. Guth. A. Düffels, G. Seidel, M. Liebl, B. Gabor, R. Mynott, Chem. Eur. J. 2001, 7, 4811-4820;
31. b) E. A. Shaffer, C. L. Chen, A. M. Beatty, E. J. Valente. H. J. Schanz. J. Organomet. Chem. 2007, 692, 5221-5233:
32. c) S. Monsaert, R. Drozdzak. V. Dragutan, I. Dragutan, F. Verpoort, Eur. J. Inorg. Chem. 2008, 432-440;
33. d) S. Monsaert, E. De Canck, R. Drozdzak. P. Van Der Voort, F. Verpoort. J. C. Martins. R. M. S. Hendrickx. Eur: J. Inorg. Chem. 2009, 655-665.
34. For a review on ruthenium-indenylidene complexes, see: F. Boeda, H. Clavier, S. P. Nolan. Chem. Commun. 2008, 2726-2740.
35. For details see the Supporting Information.
36. M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953-956.
37. a) S. B. Garber, J. S. kingsbury, B. L. Gray, A. H. Hoveyda. J. Am. Chem. Soc. 2000, 122, 8168-8179;
38. b) S. Gessler, S. Randl, S. Blechert, Tetrahedron Lett. 2000, 41, 9973-9976.
39. a) A. Fürstner. L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott. F. Stelzer, O. R. Thiel. Chem. Eur. J. 2001, 7, 3236-3253:
40. b) M. B. Dinger, J. C. Mol. Adv. Synth. Catal. 2002, 344, 671-677.
41. F. C. Courchav, J. C. Sworen, K. B. Wagener, Macromolecules 2003, 36, 8231-8239.
42. H. Clavier, F. Caijo, E. Borré, D. Rix, F. Boeda, S. R Nolan, M. Mauduit, Eur. J. Org. Chem. 2009, 4254-4265.
43. D. Fischer, S. Blechert. Adv. Synth. Catal. 2005, 347, 1329-1332.