Aluminum(salen) complexes as catalysts for the kinetic resolution of terminal epoxides via CO2 coupling

ACS Catalysis

Volumn 5, Issue 6, 2015, Pages 3398-3402

  North, Michael ^a   Quek, Sophie C Z ^a   Pridmore, Natalie E ^a   Whitwood, Adrian C ^a   Wu, Xiao ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

aluminum(salen); catalysis; cyclic carbonate; epoxide; kinetic resolution

Indexed keywords

CARBON DIOXIDE; CATALYSIS; CATALYSTS; KINETICS;

CO CATALYSTS; CYCLIC CARBONATES; EPOXIDE; KINETIC RESOLUTION; RELATIVE RATES; TERMINAL EPOXIDE; TETRABUTYLAMMONIUM BROMIDE;

ALUMINUM COMPOUNDS;

EID: 84930653433     PISSN: None     EISSN: 21555435     Source Type: Journal    
DOI: 10.1021/acscatal.5b00235     Document Type: Article

References (50)

1. Schäffner, B.; Schaffner, F.; Verevkin, S. P.; Börner, A. Chem. Rev. 2010, 110, 4554-4581 10.1021/cr900393d
2. Buysch, H. -J. In Carbonic Esters. Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH Verlag: Weinheim, 2000.
3. Doscher, P. A. Low toxicity liquid solvent. US5007969, 1991.
4. Doscher, P. A. Carbonate/diester based solvent. US5098594A, 1992.
5. Doscher-Good, P. A. Solvent with alicyclic carbonate and ethylene dipropionate. US5204026A, 1993.
6. Salvati, M. E.; Finlay, H.; Harikrishnan, L. S.; Jiang, J.; Johnson, J. A.; Kamau, M. G.; Lawrence, R. M.; Miller, M. M.; Qiao, J. X.; Wang, T. C.; Wang, Y.; Yang, W. Heterocyclic CETP inhibitors. WO2007062314A2, 2007.
7. Tunge, J. A.; Gately, D. A.; Norton, J. R. J. Am. Chem. Soc. 1999, 121, 4520-4521 10.1021/ja984061x
8. Aoyagi, N.; Furusho, Y.; Endo, T. Tetrahedron Lett. 2013, 54, 7031-7034 10.1016/j.tetlet.2013.10.068
9. Buysch, H.-J.; Krimm, H.; Böhm, S. Process for the preparation of dimethyl carbonate. EP0021211A1, 1979.
10. Romano, U.; Tesel, R.; Mauri, M. M.; Rebora, P. Ind. Eng. Chem. Prod. Res. Dev. 1980, 19, 396-403 10.1021/i360075a021
11. Sakakura, T.; Kohno, K. Chem. Commun. 2009, 1312-1330 10.1039/b819997c
12. Decortes, A.; Castilla, A. M.; Kleij, A. W. Angew. Chem., Int. Ed. 2010, 49, 9822-9837 10.1002/anie.201002087
13. North, M.; Wang, B.; Young, C. Energy Environ. Sci. 2011, 4, 4163-4170 10.1039/c1ee01074c
14. Martín, C.; Fiorani, G.; Kleij, A. W. ACS Catal. 2015, 5, 1353-1370 10.1021/cs5018997
15. Comerford, J. W.; Ingram, I. D. V.; North, M.; Wu, X. Green Chem. 2015, 17, 1966-1987 10.1039/C4GC01719F
16. Clegg, W.; Harrington, R. W.; North, M.; Pasquale, R. Chem.-Eur. J. 2010, 16, 6828-6843 10.1002/chem.201000030
17. Meléndez, J.; North, M.; Pasquale, R. Eur. J. Inorg. Chem. 2007, 2007, 3323-3326 10.1002/ejic.200700521
18. Metcalfe, I. S.; North, M.; Pasquale, R.; Thursfield, A. Energy Environ. Sci. 2010, 3, 212-215 10.1039/B918417A
19. Beattie, C.; North, M.; Villuendas, P.; Young, C. J. Org. Chem. 2012, 78, 419-426 10.1021/jo302317w
20. Davis, R. L.; Stiller, J.; Naicker, T.; Jiang, H.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2014, 53, 7406-7426 10.1002/anie.201400241
21. Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307-1315 10.1021/ja016737l
22. Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360-1362 10.1021/ja038590z
23. Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420-7421 10.1021/ja961708+
24. Nielsen, L. P. C.; Zuend, S. J.; Ford, D. D.; Jacobsen, E. N. J. Org. Chem. 2012, 77, 2486-2495 10.1021/jo300181f
25. Ford, D. D.; Nielsen, L. P. C.; Zuend, S. J.; Musgrave, C. B.; Jacobsen, E. N. J. Am. Chem. Soc. 2013, 135, 15595-15608 10.1021/ja408027p
26. Ren, W.-M.; Liu, Y.; Lu, X.-B. J. Org. Chem. 2014, 79, 9771-9777 10.1021/jo501926p
27. Brunner, M.; Mußmann, L.; Vogt, D. Synlett 1993, 1993, 893-894 10.1055/s-1993-22641
28. Brunner, M.; Mußmann, L.; Vogt, D. Synlett 1994, 1994, 69-70 10.1055/s-1994-22742
29. Aresta, M.; Dibenedetto, A.; Gianfrate, L.; Pastore, C. Appl. Catal., A 2003, 255, 5-11 10.1016/S0926-860X(03)00630-6
30. Ren, Y.; Cheng, X.; Yang, S.; Qi, C.; Jiang, H.; Mao, Q. Dalton Trans. 2013, 42, 9930-9937 10.1039/c3dt50664a
31. Paddock, R. L.; Nguyen, S. T. Chem. Commun. 2004, 1622-1623 10.1039/b401543f
32. Lu, X.-B.; Liang, B.; Zhang, Y.-J.; Tian, Y.-Z.; Wang, Y.-M.; Bai, C.-X.; Wang, H.; Zhang, R. J. Am. Chem. Soc. 2004, 126, 3732-3733 10.1021/ja049734s
33. Berkessel, A.; Brandenburg, M. Org. Lett. 2006, 8, 4401-4404 10.1021/ol061501d
34. Chang, T.; Jing, H.; Jin, L.; Qiu, W. J. Mol. Catal. A: Chem. 2007, 264, 241-247 10.1016/j.molcata.2006.08.089
35. Chen, S.-W.; Kawthekar, R. B.; Kim, G.-J. Tetrahedron Lett. 2007, 48, 297-300 10.1016/j.tetlet.2006.11.014
36. Jin, L.; Huang, Y.; Jing, H.; Chang, T.; Yan, P. Tetrahedron: Asymmetry 2008, 19, 1947-1953 10.1016/j.tetasy.2008.08.001
37. Yan, P.; Jing, H. Adv. Synth. Catal. 2009, 351, 1325-1332 10.1002/adsc.200900137
38. Chang, T.; Jin, L.; Jing, H. ChemCatChem 2009, 1, 379-383 10.1002/cctc.200900135
39. Zhang, S.; Song, Y.; Jing, H.; Yan, P.; Cai, Q. Chin. J. Catal. 2009, 30, 1255-1260 10.1016/S1872-2067(08)60143-6
40. Zhang, S.; Huang, Y.; Jing, H.; Yao, W.; Yan, P. Green Chem. 2009, 11, 935-938 10.1039/b821513h
41. Song, Y. Y.; Jin, Q. R.; Zhang, S. L.; Jing, H. W.; Zhu, Q. Q. Sci. China: Chem. 2011, 54, 1044-1050 10.1007/s11426-011-4274-2
42. Jang, D. Y.; Jang, H. G.; Kim, G. R.; Kim, G.- J. Catal. Today 2012, 185, 306-312 10.1016/j.cattod.2011.08.013
43. Roy, T.; Kureshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Bajaj, H. C. Catal. Sci. Technol. 2013, 3, 2661-2667 10.1039/c3cy00325f
44. Ren, W.-M.; Wu, G.-P.; Lin, F.; Jiang, J.-Y.; Liu, C.; Luo, Y.; Lu, X.-B. Chem. Sci. 2012, 3, 2094-2102 10.1039/c2sc20068f
45. Tanaka, H.; Kitaichi, Y.; Sato, M.; Ikeno, T.; Yamada, T. Chem. Lett. 2004, 33, 676-677 10.1246/cl.2004.676
46. Yamada, W.; Kitaichi, Y.; Tanaka, H.; Kojima, T.; Sato, M.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2007, 80, 1391-1401 10.1246/bcsj.80.1391
47. Lu, X.- B.; Ren, W.- M.; Wu, G.- P. Acc. Chem. Res. 2012, 45, 1721-1735 10.1021/ar300035z
48. Taherimehr, M.; Pescarmona, P. P. J. Appl. Polym. Sci. 2014, 41141 10.1002/app.41141
49. Darensbourg, D. J.; Yeung, A. D. Polym. Chem. 2014, 5, 3949-3962 10.1039/c4py00299g
50. CCDC deposition no. 1047180.