Pure Appl. Chem., 2009, Vol. 81, No. 11, pp. 2001-2012
http://dx.doi.org/10.1351/PAC-CON-08-10-13
Published online 2009-10-30
Onium-tagged Ru complexes as universal catalysts for olefin metathesis reactions in various media
References
- 1a. R. R. Angew. Chem., Int. Ed. 42, 4592 (2003). ( , A. H. Hoveyda. http://dx.doi.org/10.1002/anie.200300576)
- 1b. T. M. Acc. Chem. Res. 34, 18 (2001). ( , R. H. Grubbs. http://dx.doi.org/10.1021/ar000114f)
- 1c. A. Angew. Chem., Int. Ed. 39, 3012 (2000). ( . http://dx.doi.org/10.1002/1521-3773(20000901)39:17<3012::AID-ANIE3012>3.0.CO;2-G)
- 1d. R. H. Tetrahedron 54, 4413 (1998). ( , S. Chang. http://dx.doi.org/10.1016/S0040-4020(97)10427-6)
- 1e. M. Angew. Chem., Int. Ed. Engl. 36, 2037 (1997). ( , S. Blechert. http://dx.doi.org/10.1002/anie.199720361)
- 1f. V. Platinum Met. Rev. 45, 155 (2001). , I. Dragutan, A. T. Balaban.
- 2. T. Org. Process Res. Dev. 9, 513 (2005). ( , M. Brenner, K. Donsbach, P. Kreye. http://dx.doi.org/10.1021/op0580015)
- 3a. J. C. J. Am. Chem. Soc. 127, 11882 (2005). ( , H. H. Parnas, J. L. Snelgrove, D. E. Fogg. http://dx.doi.org/10.1021/ja042736s)
- 3b. For example, in a crude untreated product of diethyl diallylmalonate RCM catalyzed by 5 mol % of Grubbs I-generation catalyst, the theoretical amount of Ru is 90 mg per 5 mg of product (18 000 ppm). After filtration of the crude reaction mixture, the Ru level was reduced to 59.7 ± 0.50 mg per 5 mg (12 000 ppm). Further purification of such crude metathesis products usually reduces Ru levels below 2000 ppm, see ref. [3a] and (b) K. Org. Lett. 8, 2663 (2006). ( , D. P. Allen, A. E. Holliday, C. M. Crudden. http://dx.doi.org/10.1021/ol060389g)
- 4. Another solution to this problem might be based on the immobilization of a metathesis catalyst in a separate liquid or solid phase. For recent reviews, see.
- 4a. A. H. Org. Biomol. Chem. 2, 1 (2004). ( , D. G. Gillingham, J. J. Van Veldhuizen, O. Kataoka, S. B. Garber, J. S. Kingsbury, J. P. A. Harrity. http://dx.doi.org/10.1039/b311496c)
- 4b. R. M. New J. Chem. 28, 549 (2004); for related systems developed in our laboratories, see. ( . http://dx.doi.org/10.1039/b315236g)
- 4c. K. Synlett 2948 (2005). , K. Mennecke, U. Kunz, A. Kirschning.
- 4d. K. Tetrahedron Lett. 43, 6425 (2002). ( , M. Tryznowki, M. Bieniek. http://dx.doi.org/10.1016/S0040-4039(02)02283-9)
- 5. J. H. Org. Lett. 5, 531 (2003). ( , B. M. Kim. http://dx.doi.org/10.1021/ol027423l)
- 6. B. Cornils, W. A. Hermann (Eds.). Aqueous-Phase Organometallic Catalysis, Wiley-VCH, Weinheim (2004).
- 7. For a review on sustainable aspects of olefin metathesis, see: H. Angew. Chem., Int. Ed. 46, 6786 (2007). ( , K. Grela, A. Kirschning, M. Mauduit, S. P. Nolan. http://dx.doi.org/10.1002/anie.200605099)
- 8. For example, see.
- 8a. E. J. Nature 392, 30 (1998). ( , W. J. Sanders, L. L. Kiessling. http://dx.doi.org/10.1038/32073)
- 8b. M. J. Am. Chem. Soc. 119, 9931 (1997). ( , K. H. Mortell, L. L. Kiessling. http://dx.doi.org/10.1021/ja972089n)
- 8c. D. D. J. Am. Chem. Soc. 119, 3161 (1997). ( , X. Hu, P. Beck, L. L. Kiessling. http://dx.doi.org/10.1021/ja964046x)
- 8d. D. D. Tetrahedron 53, 11937 (1997). ( , L. E. Strong, X. Hu, P. Beck, L. L. Kiessling. http://dx.doi.org/10.1016/S0040-4020(97)00707-2)
- 9a. D. M. J. Am. Chem. Soc. 118, 784 (1996). ( , S. Kanaoka, R. H. Grubbs. http://dx.doi.org/10.1021/ja950327d)
- 9b. V. J. Am. Chem. Soc. 127, 14568 (2005). ( , P. Wehrmann, S. Mecking. http://dx.doi.org/10.1021/ja0558084)
- 10a. T. A. J. Org. Chem. 63, 9904 (1998). ( , D. M. Lynn, R. H. Grubbs. http://dx.doi.org/10.1021/jo981678o)
- 10b. K. J. J. Mol. Catal. A: Chem. 177, 173 (2002). ( , D. Sinou. http://dx.doi.org/10.1016/S1381-1169(01)00239-4)
- 10c. M. T. J. Am. Chem. Soc. 128, 14434 (2006). ( , M. B. Runge, N. B. Bowden. http://dx.doi.org/10.1021/ja0642212)
- 10d. S. J. Adv. Synth. Catal. 345, 572 (2003). ( , M. Rivard, M. Zaja, S. Blechert. http://dx.doi.org/10.1002/adsc.200202201)
- 10e. M. T. Macromol. Rapid Commun. 25, 858 (2004). ( , O. Nuyken, R. Weberskirch. http://dx.doi.org/10.1002/marc.200300297)
- 10f. for early examples of ROMP in aqueous media initiated by poorly defined Ru complexes such as RuCl3(H2O)n or Ru(H2O)6(TsO)2, see: B. M. J. Am. Chem. Soc. 110, 960 (1988). ( , R. H. Grubbs. http://dx.doi.org/10.1021/ja00211a043)
- 10g. B. M. J. Am. Chem. Soc. 110, 7542 (1988). ( , R. H. Grubbs. http://dx.doi.org/10.1021/ja00230a047)
- 10h. M. A. Macromolecules 25, 3345 (1992). ( , C. Lepetit, D. V. McGrath, B. M. Novak, R. H. Grubbs. http://dx.doi.org/10.1021/ma00039a004)
- 10i. K. H. J. Am. Chem. Soc. 118, 2297 (1996). ( , R. V. Weatherman, L. L. Kiessling. http://dx.doi.org/10.1021/ja953574q)
- 10j. B. H. Org. Lett. 10, 1325 (2008). ( , G. T. Aguinaldo, S. Ghorai, K. Voigtritter. http://dx.doi.org/10.1021/ol800028x)
- 10k. B. H. Adv. Synth. Catal. 7–8, 953 (2008). ( , S. Ghorai, G. T. Aguinaldo. http://dx.doi.org/10.1002/adsc.200800114)
- 10l. for a review on aqueous olefin metathesis, see: D. Angew. Chem., Int. Ed. 48, 442 (2009). ( , K. Grela. http://dx.doi.org/10.1002/anie.200801451)
- 11a. K. Angew. Chem., Int. Ed. 41, 4038 (2002). ( , S. Harutyunyan, A. Michrowska. http://dx.doi.org/10.1002/1521-3773(20021104)41:21<4038::AID-ANIE4038>3.0.CO;2-0)
- 11b. A. J. Am. Chem. Soc. 126, 9318 (2004). ( , R. Bujok, S. Harutyunyan, V. Sashuk, G. Dolgonos, K. Grela. http://dx.doi.org/10.1021/ja048794v)
- 12a. K. Chem. Rec. 6, 144 (2006). ( , A. Michrowska, M. Bieniek. http://dx.doi.org/10.1002/tcr.20079)
- 12b. A. Pure Appl. Chem. 80, 31 (2008). ( , K. Grela. http://dx.doi.org/10.1351/pac200880010031)
- 13. Ł. J. Mol. Catal. A: Chem. 348, 931 (2006). , A. Michrowska, R. Bujok, K. Grela.
- 14. A. J. Am. Chem. Soc. 128, 13261 (2006). ( , K. Mennecke, U. Kunz, A. Kirschning, K. Grela. http://dx.doi.org/10.1021/ja063561k)
- 15. A. Tetrahedron Lett. 49, 3019 (2008). ( , K. Harmrolfs, K. Mennecke, J. Messinger, U. Schön, K. Grela. http://dx.doi.org/10.1016/j.tetlet.2008.02.134)
- 16. A. Michrowska. PhD Thesis, Institute of Organic Chemistry, Warsaw (2006).
- 17. A. Chem. Today 24 (6), 19 (2006). , Ł. Gułajski, K. Grela.
- 18. A. Green Chem. 8, 685 (2006). ( , Ł. Gułajski, Z. Kaczmarska, K. Mennecke, A. Kirschning, K. Grela. http://dx.doi.org/10.1039/b605138c)
- 19. Ł. ChemSusChem 1, 103 (2008). ( , A. Michrowska, J. Naro?nik, Z. Kaczmarska, L. Rupnicki, K. Grela. http://dx.doi.org/10.1002/cssc.200700111)
- 20. J. B. Adv. Synth. Catal. 349, 395 (2007). ( , I. A. Guzei, R. T. Raines. http://dx.doi.org/10.1002/adsc.200600264)
- 21a. D. J. Organomet. Chem. 691, 5397 (2006). ( , H. Clavier, Ł. Gułajski, K. Grela, M. Mauduit. http://dx.doi.org/10.1016/j.jorganchem.2006.07.042)
- 21b. D. Chem. Commun. 3771 (2007). ( , F. Caïjo, I. Laurent, Ł. Gułajski, K. Grela, M. Mauduit. http://dx.doi.org/10.1039/b705451c)
- 22. J. P. Angew. Chem., Int. Ed. 46, 5152 (2007). ( , R. H. Grubbs. http://dx.doi.org/10.1002/anie.200701258)
- 23. A. Synlett 2692 (2008). ( , Ł. Gułajski, K. Mennecke, A. Meyer, T. Busch, K. Grela. http://dx.doi.org/10.1055/s-0028-1083512)
- 24. J. S. Angew. Chem., Int. Ed. 40, 4251 (2001). ( , S. B. Garber, J. M. Giftos, B. L. Gray, M. M Okamoto, R. A. Farrer, J. T. Fourkas, A. H. Hoveyda. http://dx.doi.org/10.1002/1521-3773(20011119)40:22<4251::AID-ANIE4251>3.0.CO;2-L)
- 25. E. Chomiszczak, Ł. Gułajski, K. Grela. Unpublished results.
- 26. P. Chem. Soc. Rev. 37, 2433 (2008). ( , M. Mauduit, K. Grela. http://dx.doi.org/10.1039/b711482f)