The bigger, the better: Ring-size effects of macrocyclic oligomeric Co(III)-salen catalysts

Chemical Science

Volumn 2, Issue 3, 2011, Pages 429-438

  Liu, Yu ^a   Rawlston, Jonathan ^b   Swann, Andrew T ^b   Takatani, Tait ^c   Sherrill, C David ^c   Ludovice, Peter J ^b   Weck, Marcus ^a  

^a NEW YORK UNIVERSITY   (United States)

^b Georgia Institute of Technology   (United States)

^c GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE CATALYST; ALLYL GLYCIDYL ETHERS; BIMETALLIC COMPLEXES; CATALYST LOADINGS; CATALYST SYNTHESIS; CATALYTIC ACTIVITY; CATALYTIC EFFICIENCIES; CATALYTIC TESTS; COMPUTATIONAL MODELING; CYCLOOCTENE; EPOXIDE RING-OPENING REACTION; HEXAMERS; HYDROLYTIC KINETIC RESOLUTION; MACROCYCLICS; NMR STUDIES; OLEFIN METATHESIS; PURIFICATION PROTOCOL; RING OPENING; RING SIZES; SALEN COMPLEX; SIZE EFFECTS; TERMINAL EPOXIDE; TETRAMERS;

CATALYST SELECTIVITY; COBALT COMPOUNDS; DIMERS; ETHERS; MIXTURES; OLEFINS; REACTION RATES; SYNTHESIS (CHEMICAL);

CATALYST ACTIVITY;

EID: 79955605425     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c0sc00517g     Document Type: Article

References (49)

1. R. A. Copeland, Enzymes. A practical introduction to structure, mechanism, and data analysis, John Wiley & Sons Inc., 2000.
2. J.W.A.J.L. Steed, Supramolecular Chemistry, John Wiley & Sons Inc., 2000.
3. M. Komiyama, Prog. Polym. Sci., 1993, 18, 871-898.
4. A. J. Kirby, Angew. Chem., Int. Ed. Engl., 1996, 35, 707-724.
5. J. K. M. Sanders, Chem.-Eur. J., 1998, 4, 1378-1383.
6. F. Diederich, G. Schurmann and I. Chao, J. Org. Chem., 1988, 53, 2744-2757.
7. Z. Clyde-Watson, A. Vidal-Ferran, L. J. Twyman, C. J. Walter, D. W. J. McCallien, S. Fanni, N. Bampos, R. S. Wylie and J. K. M. Sanders, New J. Chem., 1998, 22, 493-502.
8. E. N. Jacobsen, Acc. Chem. Res., 2000, 33, 421-431.
9. M. Tokunaga, J. F. Larrow, F. Kakiuchi and E. N. Jacobsen, Science, 1997, 277, 936-938.
10. S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow and E. N. Jacobsen, J. Am. Chem. Soc., 2002, 124, 1307-1315.
11. L. P. C. Nielsen, C. P. Stevenson, D. G. Blackmond and E. N. Jacobsen, J. Am. Chem. Soc., 2004, 126, 1360-1362.
12. D. A. Annis and E. N. Jacobsen, J. Am. Chem. Soc., 1999, 121, 4147-4154.
13. Y. M. Song, X. Q. Yao, H. L. Chen, C. M. Bai, X. Q. Hu and Z. Zheng, Tetrahedron Lett., 2002, 43, 6625-6627.
14. M. A. Kwon and G. J. Kim, Catal. Today, 2003, 87, 145-151.
15. M. Beigi, S. Roller, R. Haag and A. Liese, Eur. J. Org. Chem., 2008, 2135-2141.
16. X. L. Zheng, C. W. Jones and M. Weck, Adv. Synth. Catal., 2008, 350, 255-261.
17. B. M. Rossbach, K. Leopold and R. Weberskirch, Angew. Chem., Int. Ed., 2006, 45, 1309-1312.
18. R. Breinbauer and E. N. Jacobsen, Angew. Chem., Int. Ed., 2000, 39, 3604-3607.
19. J. M. Ready and E. N. Jacobsen, J. Am. Chem. Soc., 2001, 123, 2687-2688.
20. X. L. Zheng, C. W. Jones and M. Weck, J. Am. Chem. Soc., 2007, 129, 1105-1112.
21. P. Goyal, X. L. Zheng and M. Weck, Adv. Synth. Catal., 2008, 350, 1816-1822.
22. X. F. Guo, Y. S. Kim and G. J. Kim, Top. Catal., 2009, 52, 153-160.
23. C. S. Gill, W. Long and C. W. Jones, Catal. Lett., 2009, 131, 425-431.
24. X. Zhu, K. Venkatasubbaiah, M. Weck and C. W. Jones, ChemCatChem, 2010, 2, 1252-1259.
25. J. M. Ready and E. N. Jacobsen, Angew. Chem., Int. Ed., 2002, 41, 1374-1377.
26. R. N. Loy and E. N. Jacobsen, J. Am. Chem. Soc., 2009, 131, 2786-2787.
27. D. E. White and E. N. Jacobsen, Tetrahedron: Asymmetry, 2003, 14, 3633-3638.
28. J. Hine and R. L. Flachska., J. Org. Chem., 1974, 39, 863-870.
29. J. M. Notestein and A. Katz, Chem.-Eur. J., 2006, 12, 3954-3965.
30. J. D. Bass, A. Solovyov, A. J. Pascall and A. Katz, J. Am. Chem. Soc., 2006, 128, 3737-3747.
31. N. Madhavan, C. W. Jones and M. Weck, Acc. Chem. Res., 2008, 41, 1153-1165.
32. S. Kemper, P. Hrobarik, M. Kaupp and N. E. Schloerer, J. Am. Chem. Soc., 2009, 131, 4172-4173.
33. H. Gunther and G. Jikeli, Chem. Rev., 1977, 77, 599-637.
34. Interconversion between cis- and trans-isomers of cyclic monoene or diene have been thoroughly studied via Variable Temperature NMR. The conversion temperatures range from room temperature to over 200 °C depending on the ring size, structure and modification. With the same ring size, the interconversion of cyclic diene is much easier than the corresponding cyclic monoene due to the lower racemization energy barrier.
35. H. Gunther and G. Jikeli, Chem. Rev., 1977, 77, 599-637 and for the cyclic monoene and cyclic diene comparison see:
36. C. B. Reese and A. Shaw, Chem. Commun., 1970, 1367-1368.
37. T. A. Halgren, J. Comput. Chem., 1996, 17, 490-519.
38. S. H. Shi, L. Yan, Y. Yang, J. Fisher-Shaulsky and T. Thacher, J. Comput. Chem., 2003, 24, 1059-1076.
39. K. Malek, A. P. J. Jansen, C. Li and R. A. van Santen, J. Catal., 2007, 246, 127-135.
40. W. H. Leung, E. Y. Y. Chan, E. K. F. Chow, I. D. Williams and S. M. Peng, J. Chem. Soc., Dalton Trans., 1996, 1229-1236.
41. J. J. Chapman, C. S. Day and M. E. Welker, Eur. J. Org. Chem., 2001, 2273-2282.
42. C. T. Cohen, C. M. Thomas, K. L. Peretti, E. B. Lobkovsky and G. W. Coates, Dalton Trans., 2006, 237-249.
43. B. L. Holian, A. J. Degroot, W. G. Hoover and C. G. Hoover, Phys. Rev. A, 1990, 41, 4552-4553.
44. The distance between two Co centers for a possible reaction has not been determined experimentally or theoretically. Here, 10 Å was chosen because it is approximately the separation of the catalyst sites due to the acetate counter ion commonly used in these catalyst systems. A sensitivity analysis of this separation distance showed that this distance was also reasonably sensitive to the occurrence of potential reaction events as a function of macrocyclic octane geometries.
45. M. Wojciechowski and B. Lesyng, J. Phys. Chem. B, 2004, 108, 18368-18376.
46. J. A. Dean, Lange's Handbook of Chemistry, McGraw-Hill Professional, 1998.
47. K. Nozaki, K. Nakano and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 11008-11009.
48. S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi and M. Shibasaki, J. Am. Chem. Soc., 2000, 122, 2252-2260.
49. J. Hine and F. A. Via, J. Am. Chem. Soc., 1972, 94, 190-194.