Phase transfer activation of fluorous analogs of Grubbs second-generation catalyst: Ring-opening metathesis polymerization

ACS Catalysis

Volumn 2, Issue 1, 2012, Pages 155-162

  Tuba, Robert ^a   Corrêa Da Costa, Rosenildo ^b   Bazzi, Hassan S ^a   Gladysz, John A ^c  

^a TEXAS A AND M UNIVERSITY AT QATAR   (Qatar)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^c TEXAS A AND M UNIVERSITY   (United States)

Author keywords

biphase catalysis; fluorous; Grubbs' catalyst; phase transfer; polynorbornene; ROMP

Indexed keywords

FLUOROUS; GRUBBS' CATALYST; PHASE TRANSFER; POLYNORBORNENES; ROMP;

CATALYSTS; GLASS TRANSITION; OLEFINS; PHOSPHORUS COMPOUNDS; POLYDISPERSITY;

RING OPENING POLYMERIZATION;

EID: 84855579356     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs200487j     Document Type: Article

References (44)

1. Yoshida, J.-i.; Itami, K. Chem. Rev. 2002, 102, 3693
2. Shaughnessy, K. H. Chem. Rev. 2009, 109, 643
3. Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horváth, I. T., Eds.; Wiley/VCH: Weinheim, 2004.
4. Pinault, N.; Bruce, D. W. Coord. Chem. Rev. 2003, 241, 1
5. Snelders, D. J. M.; van Koten, G.; Gebbink, R. J. M K. Chem.-Eur. J. 2011, 17, 42
6. Gudmunsen., D.; Hope, E. G.; Paige, D. R.; Stuart, A. M. J. Fluorine Chem. 2009, 130, 942
7. Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324
8. Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543
9. Love, J. A.; Sanford, M. S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 10103
10. Correa da Costa, R.; Gladysz, J. A. Chem. Commun. 2006, 2619
11. Correa da Costa, R.; Gladysz, J. A. Adv. Synth. Catal. 2007, 349, 243
12. Alvey, L. J.; Rutherford, D.; Juliette, J. J. J.; Gladysz, J. A. J. Org. Chem. 1998, 63, 6302
13. Gladysz, J. A.; Emnet, C.; Rábai, J. Partition Coefficients involving Fluorous Solvents. In Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horváth, I. T., Eds.; Wiley/VCH: Weinheim, 2004; pp 56-100.
14. Xi, Z.; Bazzi, H. S.; Gladysz, J. A. Org. Lett. 2011, 13, 6188
15. Bielawski, C. W.; Grubbs, R. H. Angew. Chem., Int. Ed. 2000, 39, 2903
16. Angew. Chem. 2000, 112, 3025.
17. Bielawski, C. W.; Benitez, D.; Morita, T.; Grubbs, R. H. Macromolecules 2001, 34, 8610
18. Vargas, J.; Colin, E. S.; Tlenkopatchev, M. A. Eur. Polym. J. 2004, 40, 1325 (for the generation of 6 using 2, see the first entries in Tables 24 therein)
19. See also: Buchmeiser, M. R.; Ahmad, I.; Gurram, V.; Kumar, P. S. Macromolecules 2011, 44, 4098
20. For earlier reports of ROMP polymers generated from this monomer, see refs 21-24 and Bazzi, H. S.; Bouffard, J.; Sleiman, H. F. Macromolecules 2003, 36, 7899
21. Metera, K. L.; Sleiman, H. Macromolecules 2007, 40, 3733
22. Lo, P. K.; Sleiman, H. F. J. Am. Chem. Soc. 2009, 131, 4182
23. Gabriel, G. J.; Maegerlein, J. A.; Nelson, C. F.; Dabkowski, J. M.; Eren, T.; Nüsslein, K.; Tew, G. N. Chem.-Eur. J. 2009, 15, 433
24. Sankaran, N. B.; Rys, A. Z.; Nassif, R.; Nayak, M. K.; Metera, K.; Chen, B.; Bazzi, H. S.; Sleiman, H. F. Macromolecules 2010, 43, 5530
25. Correa da Costa, R. doctoral thesis, Universität Erlangen-Nürnberg, 2006.
26. Gladysz, J. A. The Experimental Assay of Catalyst Recovery: General Concepts. In Recoverable and Recyclable Catalysts; Benanglia, M., Ed; Wiley-Blackwell: Oxford, England, 2009; pp 1-22.
27. Black, G.; Maher, D.; Risse, W. Living Ring-Opening Olefin Metathesis Polymerization. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley/VCH: Weinheim, 2003; Vol. 3; pp 2-71; (see especially section 3.2.4.8).
28. Bielawski, C. W.; Grubbs, R. H. Prog. Polym. Sci. 2007, 32, 1
29. Buchowicz, W.; Holerca, M. N.; Percec, V. Macromolecules 2001, 34, 3842
30. Rost, D.; Porta, M.; Gessler, S.; Blechert, S. Tetrahedron Lett. 2008, 49, 5968
31. Samojłowicz, C.; Bieniek, M.; Zarecki, A.; Kadyrov, R.; Grela, K. Chem. Commun. 2008, 6282
32. Grandbois, A.; Collins, S. K. Chem.-Eur. J. 2008, 14, 9323
33. Ritter, T.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 11768
34. Siano, V.; D'Auria, I.; Grisi, F.; Constable, C.; Longo, P. Cent. Eur. J. Chem. 2011, 9, 605
35. Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153
36. Lynn, D. M.; Mohr, B.; Grubbs, R. H.; Henling, L. M.; Day, M. W. J. Am. Chem. Soc. 2000, 122, 6601
37. Sanford, M. S.; Henling, L. M.; Grubbs, R. H. Organometallics 1998, 17, 5384
38. Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887
39. Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375
40. Rivard, M.; Blechert, S. Eur. J. Org. Chem. 2003, 2225
41. See also: Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168
42. See also: Bieniek, M.; Samojłowicz, C.; Sashuk, V.; Bujok, R.; Śledź, P.; Lugan, N.; Lavigne, G.; Arlt, D.; Grela, K. Organometallics 2011, 30, 4144
43. Dunbar, M. A.; Balof, S. L.; Roberts, A. N.; Valente, E. J.; Schanz, H.-J. Organometallics 2011, 30, 199 and earlier work cited therein
44. Clevenger, R. C.; Turnbull, K. D. Synth. Commun. 2000, 30, 1379