Enantioselective polymerization of epoxides using biaryl-linked bimetallic cobalt catalysts: A mechanistic study

Journal of the American Chemical Society

Volumn 135, Issue 50, 2013, Pages 18901-18911

  Ahmed, Syud M ^a   Poater, Albert ^b,c   Childers, M Ian ^a   Widger, Peter C B ^a   Lapointe, Anne M ^a   Lobkovsky, Emil B ^a   Coates, Geoffrey W ^a   Cavallo, Luigi ^c  

^a Department of Obstetrics Gynecology   (United States)

^b UNIVERSITY OF GIRONA   (Spain)

^c KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE STEREOCHEMISTRY; BIMETALLIC CATALYSTS; CARBOXYLATE LIGANDS; CATALYTIC SYSTEM; MECHANISTIC STUDIES; STEREO-SELECTIVE; STRUCTURAL FEATURE; STRUCTURAL INFORMATION;

CARBOXYLATION; CATALYTIC OXIDATION; CHAINS; CHLORINE COMPOUNDS; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; LIGANDS; POLYMERIZATION; POLYMERS; POLYOLS; PROPYLENE; STEREOSELECTIVITY;

CATALYSTS;

COBALT DERIVATIVE; EPOXIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPYLENE OXIDE;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; POLYMERIZATION; RING OPENING; STEREOCHEMISTRY;

EID: 84890735205     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja409521z     Document Type: Article

References (60)

1. For a review, see: Ajiro, H.; Widger, P. C. B.; Ahmed, S. M.; Allen, S. D.; Coates, G. W. Stereoselective Ring-Opening of Epoxides. In Polymer Science: A Comprehensive Reference; Matyjaszewski, K., Möller, M., Eds.; Elsevier: Amsterdam, 2012; pp 165-181.
2. Takeda, N.; Inoue, S. Makromol. Chem. 1978, 179, 1377-1381
3. Borgne, A. L.; Spassky, N.; Jun, C. L.; Momtaz, A. Makromol. Chem. 1988, 189, 637-650
4. Yoshino, N.; Suzuki, C.; Kobayashi, H.; Tsuruta, T. Makromol. Chem. 1988, 189, 1903-1913
5. Hasebe, Y.; Tsuruta, T. Makromol. Chem. 1988, 189, 1915-1926
6. Vincens, V.; Borgne, A. L.; Spassky, N. Makromol. Chem. Rapid Commun. 1989, 10, 623-628
7. Pruitt, M. E.; Baggett, J. M. (Dow Chemical Co.). Catalysts for the Polymerization of Olefin Oxides. U.S. Patent 2,706,181, 1955.
8. Pruitt, M. E.; Baggett, J. M.; Bloomfield, R. J.; Templeton, J. H. (Dow Chemical Co.). Polymerization of Olefin Oxides. U.S. Patent 2,706,182, 1955.
9. Pruitt, M. E.; Baggett, J. M. (Dow Chemical Co.). Solid Polymers of Propylene Oxide. U.S. Patent 2,706,189, 1955.
10. Price, C. C.; Osgan, M.; Hughes, R. E.; Shambelan, C. J. Am. Chem. Soc. 1956, 78, 690-691
11. Price, C. C.; Osgan, M. J. Am. Chem. Soc. 1956, 78, 4787-4792
12. Vandenberg, E. J. J. Polym. Sci. 1960, 47, 486-489
13. Vandenberg, E. J. (Hercules Powder Co.). Organoaluminum Oxide Catalyst Composition. U.S. Patent 3,219,591, 1965.
14. Vandenberg, E. J. J. Polym. Sci., Part A: Polym. Chem. 1969, 7, 525-567
15. Vandenberg, E. J. J. Polym. Sci., Part A: Polym. Chem. 1986, 24, 1423-1431
16. Vandenberg, E. J. Polymer 1994, 35, 4933-4939
17. Peretti, K. L.; Ajiro, H.; Cohen, C. T.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2005, 127, 11566-11567
18. Ajiro, H.; Peretti, K. L.; Lobkovsky, E. B.; Coates, G. W. Dalton Trans. 2009, 8828-8830
19. Hirahata, W.; Thomas, R. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2008, 130, 17658-17659
20. Thomas, R. M.; Widger, P. C. B.; Ahmed, S. M.; Jeske, R. C.; Hirahata, W.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2010, 132, 16520-16525
21. Widger, P. C. B.; Ahmed, S. M.; Coates, G. W. Macromolecules 2011, 44, 5666-5670
22. Widger, P. C. B.; Ahmed, S. M.; Hirahata, W.; Thomas, R. M.; Lobkovsky, E. B.; Coates, G. W. Chem. Commun. 2010, 46, 2935-2937
23. Liu, J.; Bao, Y.-Y.; Liu, Y.; Ren, W.-M.; Lu, X.-B. Polym. Chem. 2013, 4, 1439-1444
24. Liu, Y.; Ren, W.-M.; Liu, J.; Lu, X.-B. Angew. Chem., Int. Ed. 2013, 52, 11594-11598
25. Ragone, F.; Poater, A.; Cavallo, L. J. Am. Chem. Soc. 2010, 132, 4249-4258
26. Poater, A.; Ragone, F.; Mariz, R.; Dorta, R.; Cavallo, L. Chem.-Eur. J. 2010, 16, 14348-14353
27. Hillier, A. C.; Sommer, W. J.; Yong, B. S.; Petersen, J. L.; Cavallo, L.; Nolan, S. P. Organometallics 2003, 22, 4322-4326
28. Viciu, M. S.; Navarro, O.; Germaneau, R. F.; Kelly, R. A.; Sommer, W.; Marion, N.; Stevens, E. D.; Cavallo, L.; Nolan, S. P. Organometallics 2004, 23, 1629-1635
29. Poater, A.; Cosenza, B.; Correa, A.; Giudice, S.; Ragone, F.; Scarano, V.; Cavallo, L. Eur. J. Inorg. Chem. 2009, 1759-1766
30. Kemper, S.; Hrobárik, P.; Kaupp, M.; Schlörer, N. E. J. Am. Chem. Soc. 2009, 131, 4172-4173
31. Ford, D. D.; Nielsen, L. P. C.; Zuend, S. J.; Musgrave, C. B.; Jacobsen, E. N. J. Am. Chem. Soc. 2013, 135, 15595-15608
32. Coates, G. W. Chem. Rev. 2000, 100, 1223-1252
33. Resconi, L.; Cavallo, L.; Fait, A.; Piemontesi, F. Chem. Rev. 2000, 100, 1253-1346
34. Gansäuer, A.; Barchuk, A.; Keller, F.; Schmitt, M.; Grimme, S.; Gerenkamp, M.; Mück-Lichtenfeld, C.; Daasbjerg, K.; Svith, H. J. Am. Chem. Soc. 2007, 129, 1359-1371
35. Debuigne, A.; Poli, R.; Jéroîme, C.; Jéroîme, R.; Detrembleur, C. Prog. Polym. Sci. 2009, 34, 211-239
36. Cavallo, L.; Jacobsen, H. J. Phys. Chem. A 2003, 107, 5466-5471
37. Jacobsen, H.; Cavallo, L. Phys. Chem. Chem. Phys. 2004, 6, 3747-3753
38. Bozoglian, F.; Romain, S.; Ertem, M. Z.; Todorova, T. K.; Sens, C.; Mola, J.; Rodriguez, M.; Romero, I.; Benet-Buchholz, J.; Fontrodona, X.; Cramer, C. J.; Gagliardi, L.; Llobet, A. J. Am. Chem. Soc. 2009, 131, 15176-15187
39. Aida, T.; Inoue, S. J. Am. Chem. Soc. 1985, 107, 1358-1364
40. Aida, T.; Ishikawa, M.; Inoue, S. Macromolecules 1986, 19, 8-13
41. Aida, T.; Inoue, S. Acc. Chem. Res. 1996, 29, 39-48
42. Lu, X.-B.; Wang, Y. Angew. Chem., Int. Ed. 2004, 43, 3574-3577
43. Darensbourg, D. J.; Billodeaux, D. R. Inorg. Chem. 2005, 44, 1433-1442
44. Darensbourg, D. J.; Phelps, A. L. Inorg. Chem. 2005, 44, 4622-4629
45. Cohen, C. T.; Chu, T.; Coates, G. W. J. Am. Chem. Soc. 2005, 127, 10869-10878
46. Cohen, C. T.; Coates, G. W. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 5182-5191
47. Sugimoto, H.; Kuroda, K. Macromolecules 2008, 41, 312-317
48. Nakano, K.; Hashimoto, S.; Nozaki, K. Chem. Sci. 2010, 1, 369-373
49. Hosseini Nejad, E.; van Melis, C. G. W.; Vermeer, T. J.; Koning, C. E.; Duchateau, R. Macromolecules 2012, 45, 1770-1776
50. Linde, C.; Arnold, M.; Åkermark, B.; Norrby, P.-O. Angew. Chem., Int. Ed. 1997, 36, 1723-1725
51. Strassner, T.; Houk, K. N. Org. Lett. 1999, 1, 419-422
52. Cavallo, L.; Jacobsen, H. Angew. Chem., Int. Ed. 2000, 39, 589-592
53. Abashkin, Y. G.; Collins, J. R.; Burt, S. K. Inorg. Chem. 2001, 40, 4040-4048
54. Linde, C.; Koliaï, N.; Norrby, P.-O.; Åkermark, B. Chem.-Eur. J. 2002, 8, 2568-2573
55. Adam, W.; Roschmann, K. J.; Saha-Möller, C. R.; Seebach, D. J. Am. Chem. Soc. 2002, 124, 5068-5073
56. Cavallo, L.; Jacobsen, H. Eur. J. Inorg. Chem. 2003, 2003, 892-902
57. Cavallo, L.; Jacobsen, H. Inorg. Chem. 2004, 43, 2175-2182
58. Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360-1362
59. Nielsen, L. P. C.; Zuend, S. J.; Ford, D. D.; Jacobsen, E. N. J. Org. Chem. 2012, 77, 2486-2495
60. Braune, W.; Okuda, J. Angew. Chem., Int. Ed. 2003, 42, 64-68