A green catalyst for green chemistry: Synthesis and application of an olefin metathesis catalyst bearing a quaternary ammonium group

Green Chemistry

Volumn 8, Issue 8, 2006, Pages 685-688

  Michrowska, Anna ^a   Gułajski, Łukasz ^a,b   Kaczmarska, Zuzanna ^a,c   Mennecke, Klaas ^d   Kirschning, Andreas ^d   Grela, Karol ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

^c UNIVERSITY OF WARSAW   (Poland)

^d LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746823357     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b605138c     Document Type: Article

References (38)

1. Pertinent reviews: R. H. Grubbs, Handbook of Metathesis, Wiley-VCH, Weinheim, 2003, vol. 1–3.
2. T. M. Trnka R. H. Grubbs Acc. Chem. Res. 2001 34 18.
3. A. Fürstner Angew. Chem. 2000 112 3140.
4. Angew. Chem., Int. Ed. 2000 39 3012.
5. R. H. Grubbs S. Chang Tetrahedron 1998 54 4413.
6. M. Schuster S. Blechert Angew. Chem. 1997 109 2124.
7. T. Nicola M. Brenner K. Donsbach P. Kreye Org. Process Res. Dev. 2005 9 513.
8. J. C. Conrad H. H. Parnas J. L. Snelgrove D. E. Fogg J. Am. Chem. Soc. 2005 127 11882.
9. For example, in a crude untreated product of diethyl diallylmalonate (12c) RCM catalysed by 5 mol% of Grubbs I-generation catalyst the theoretical amount of Ru is 90 μg per 5 mg of product (18 000 ppm, see Ref. 7). After filtration of the crude reaction mixture, the Ru level was reduced to 59.7 ± 0.50 μg per 5 mg (12 000 ppm). Further purification of such crude metathesis products usually reduces ruthenium levels below 2000 ppm, see ibid, and K. McEleney D. P. Allen A. E. Holliday C. M. Crudden Org. Lett. 2006 8 2663.
10. Another solution to this problem might be based on the immobilisation of a metathesis catalysts in a separate liquid or solid phase. For recent reviews, see: A. H. Hoveyda D. G. Gillingham J. J. Van Veldhuizen O. Kataoka S. B. Garber J. S. Kingsbury J. P. A. Harrity Org. Biomol. Chem. 2004 2 1.
11. R. M. Buchmeiser New J. Chem. 2004 28 549.
12. For related systems developed in our laboratories, see: K. Grela K. Mennecke U. Kunz A. Kirschning Synlett 2005 2948.
13. K. Grela M. Tryznowki M. Bieniek Tetrahedron Lett. 2002 43 6425.
14. Boehringer Ingelheim International GmbH, World Pat. WO 2004/089974 A1, 2004.
15. L. A. Paquette J. D. Schloss I. Efremov F. Fabris F. Gallou J. Mendez-Andino J. Yang Org. Lett. 2000 2 1259.
16. Y. M. Ahn K. Yang G. I. Georg Org. Lett. 2001 3 1411.
17. H. Maynard R. H. Grubbs Tetrahedron Lett. 1999 40 4137.
18. M. Westhus E. Gonthier D. Brohm R. Breinbauer Tetrahedron Lett. 2004 45 3141.
19. J. H. Cho B. M. Kim Org. Lett. 2003 5 531.
20. For a technical data sheet on the application of QuadraPure™ resins, see: Avecia Pharmaceuticals, http://www.quadrapure.com.
21. K. Grela M. Kim Eur. J. Org. Chem. 2003 963.
22. A. Michrowska L. Gulajski K. Grela Chem. Commun. 2006 841.
23. A. Michrowska, PhD Thesis, Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland, 2006.
24. L. Gulajski A. Michrowska R. Bujok K. Grela J. Mol. Catal. A: Chem., in print.
25. K. Grela S. Harutyunyan A. Michrowska Angew. Chem., Int. Ed. 2002 41 4038-4040.
26. A. Michrowska R. Bujok S. Harutyunyan V. Sashuk G. Dolgonos K. Grela J. Am. Chem. Soc. 2004 126 9318-9325.
27. S. Harutyunyan, A. Michrowska and K. Grela, in Catalysts for Fine Chemical Synthesis; ed. S. M. Roberts, J. Whittall, P. Mather, P. McCormack, Wiley-Interscience, New York, 2004, vol. 3, ch. 9.1, pp. 169–173.
28. A. Fürstner M. Liebl C. Lehmann M. Piquet R. Kunz C. Bruneau D. Touchard P. H. Dixneuf Chem.–Eur. J. 2000 6 10 1847.
29. D. M. Lynn B. Mohr R. H. Grubbs L. M. Henling M. W. Day J. Am. Chem. Soc. 2000 122 6601.
30. Attempts to carry out the quaternisation of another easily available precursor 10𠄲 [ref.13b] proved unsuccesful.
31. C.-J. Li Chem. Rev. 1993 93 2023.
32. C.-J. Li and T.-H. Chen, Organic Reaction in Aqueous Media, Wiley, New York, 1997.
33. P. A. Grieco, Organic Synthesis in Water, Blackie Academic & Professional, London, 1998.
34. S. Kobayashi K. Manabe Pure Appl. Chem. 2000 72 1373.
35. B. Mohr D. M. Lynn R. H. Grubbs Organometallics 1996 15 4317.
36. S. J. Connon S. Blechert Bioorg. Med. Chem. Lett. 2002 12 1873.
37. S. J. Connon M. Rivard M. Zaja S. Blechert Adv. Synth. Catal. 2003 345 572.
38. T. Rölle R. H. Grubbs Chem. Commun. 2002 1070.