Co(III)-porphyrin-mediated highly regioselective ring-opening of terminal epoxides with alcohols and phenols

ACS Catalysis

Volumn 1, Issue 5, 2011, Pages 489-492

  Venkatasubbaiah, Krishnan ^a   Zhu, Xunjin ^a   Kays, Elizabeth ^a   Hardcastle, Kenneth I ^b   Jones, Christopher W ^a  

^a Georgia Institute of Technology   (United States)

^b EMORY UNIVERSITY   (United States)

Author keywords

aryloxy alcohols; alkoxy alcohols; co porphyrin; epoxides; ring opening

Indexed keywords

CO-PORPHYRIN; EPOXIDES; REGIO-SELECTIVE; RING OPENING; TERMINAL EPOXIDE;

CATALYSTS; DIMERS; PORPHYRINS; REGIOSELECTIVITY;

PHENOLS;

EID: 79955920741     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs200114x     Document Type: Article

References (42)

1. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59 (4) 737
2. Smith, J. G. Synthesis-Stuttgart 1984, 8) 629
3. Yadav, J. S.; Reddy, B. V. S.; Harikishan, K.; Madan, C.; Narsaiah, A. V. Synthesis-Stuttgart 2005, 17) 2897
4. Haak, R. M.; Belmonte, M. M.; Escudero-Adan, E. C.; Benet-Buchholz, J.; Kleij, A. W. Dalton Transactions 2010, 39 (2), 593.
5. Bonini, C.; Righi, G. Synthesis-Stuttgart 1994, 3) 225
6. Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetrahedron Lett. 1991, 32 (36) 4775
7. Fulop, F.; Huber, I.; Bernath, G.; Honig, H.; Seuferwasserthal, P. Synthesis-Stuttgart 1991, 1) 43
8. Iranpoor, N.; Shekarriz, M. Synth. Commun. 1999, 29 (13) 2249
9. Reddy, L. R.; Reddy, M. A.; Bhanumathi, N.; Rao, K. R. New J. Chem. 2001, 25 (2) 221
10. Tanabe, K. K.; Cohen, S. M. Inorg. Chem. 2010, 49 (14) 6766
11. Darensbourg, D. J.; Moncada, A. I. Macromolecules 2009, 42 (12) 4063
12. Hirahata, W.; Thomas, R. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2008, 130 (52) 17658
13. Hartung, J.; Drees, S.; Greb, M.; Schmidt, P.; Svoboda, I.; Fuess, H.; Murso, A.; Stalke, D. Eur. J. Org. Chem. 2003, 2003 (13) 2388
14. Sugimoto, H.; Kuroda, K. Macromolecules 2008, 41 (2) 312
15. Keilitz, J.; Haag, R. Eur. J. Org. Chem. 2009, 19, 3272
16. Dhakshinamoorthy, A.; Alvaro, M.; Garcia, H., Chem. - Eur. J. 2010, 16 (28), 8530.
17. Terblans, Y. M.; Huyser, J. J.; Huyser, M.; Green, M. J.; Young, D. A.; Sibiya, M. S. Can. J. Chem. - Rev. Can. Chim. 2005, 83 (6-7) 854
18. Iranpoor, N.; Firouzabadi, H.; Safavi, A.; Shekarriz, M. Synth. Commun. 2002, 32 (15) 2287
19. Surendra, K.; Krishnaveni, N. S.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68 (12) 4994
20. Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; The Porphyrin Handbook; Academic Press: San Diego, CA, 2000-2003; Vol. 1-20.
21. Merlau, M. L.; Grande, W. J.; Nguyen, S. T.; Hupp, J. T. J. Mol. Catal. A: Chem. 2000, 156 (1-2) 79
22. Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Mohammadpoor-Baltork, I.; Taghavi, S. A. Catal. Commun. 2007, 8, 2087
23. Doyle, M. P. Angew. Chem., Int. Ed. 2009, 48 (5) 850
24. Rowley, J. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2007, 129 (16) 4948
25. Lee, M. Y.; Chen, Y.; Zhang, X. P. Organometallics 2003, 22 (24) 4905
26. Monnereau, C.; Ramos, P. H.; Deutman, A. B. C.; Elemans, J.; Nolte, R. J. M.; Rowan, A. E. J. Am. Chem. Soc. 2010, 132 (5) 1529
27. Venkatasubbaiah, K.; Gill, C. S.; Takatani, T.; Sherrill, C. D.; Jones, C. W. Chem. - Eur. J. 2009, 15, 3951
28. Zheng, X. L.; Jones, C. W.; Weck, M. Adv. Synth. Catal. 2008, 350 (2) 255
29. Gill, C. S.; Long, W.; Jones, C. W. Catal. Lett. 2009, 131, 425
30. Venkatasubbaiah, K.; Zhu, X.; Jones, C. W. Top. Catal. 2010, 53, 1063
31. Zhu, X.; Venkatasubbaiah, K.; Weck, M.; Jones, C. W. J. Mol. Catal. A: Chem. 2010, 329, 1
32. Zhu, X.; Venkatasubbaiah, K.; Weck, M.; Jones, C. W. ChemCatChem 2010, 2, 1252
33. Gill, C. S.; Venkatasubbaiah, K.; Phan, N. T. S.; Weck, M.; Jones, C. W. Chem. - Eur. J. 2008, 14 (24) 7306
34. Kamal, A.; Ahmed, S. K.; Sandbhor, M.; Khan, M. N. A.; Arifuddin, M. Chem. Lett. 2005, 34 (8) 1142
35. Ready, J. M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41 (8) 1374
36. Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123 (11) 2687
37. Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121 (25) 6086
38. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112 (14) 5525
39. Kano, K.; Minamizono, H.; Kitae, T.; Negi, S. J. Phys. Chem. A 1997, 101 (34) 6118
40. 6 and is ca. 7.4. This Co-Co distance is similar to the value (around 6) that was found in the naphthyl-based Co-salen dimer by Coates et al. (12) that was demonstrated to have high activity in the cooperative enantioselective polymerization of epoxides.
41. Jain, S.; Venkatasubbaiah, K.; Jones, C. W.; Davis, R. J. J. Mol. Catal. A: Chem. 2010, 316 (1-2) 8
42. Little, R. G. J. Heterocyc. Chem. 1978, 15 (2) 203