In situ generation of the coates catalyst: A practical and versatile catalytic system for the carbonylation of meso-epoxides

Organic Letters

Volumn 13, Issue 12, 2011, Pages 3142-3145

  Ganji, Prasad ^a   Doyle, David J ^a   Ibrahim, Hasim ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79958793967     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201043d     Document Type: Article

References (35)

1. For reviews, see: Church, T. L.; Getzler, Y. D. Y. L.; Byrne, C. M.; Coates, G. W. Chem. Commun. 2007, 657-674
2. Nakano, K.; Nazoki, K. Top. Organomet. Chem. 2006, 18, 223-238
3. Deng, F.-G.; Hu, B.; Sun, W.; Chen, J.; Xia, C.-G. Dalton. Trans. 2007, 4262-4267
4. Denmark, S. E.; Ahmad, M. J. Org. Chem. 2007, 72, 9630-9634
5. Kim, H. S.; Bae, J. Y.; Lee, J. S.; Jeong., C., II; Choi, D. K.; Kang, S. O.; Cheong, M. Appl. Catal., A: Gen. 2006, 301, 75
6. Hinterding, K.; Jacobsen J. Org. Chem. 1999, 64, 2164-2165
7. Goodman, S. N.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 4703-4705
8. Watanabe, Y.; Nishiyama, K.; Zhang, K.; Okuda, F.; Kondo, T.; Tsuji, Y. Bull. Chem. Soc. Jpn. 1994, 67, 879-882
9. For reviews on β-lactones, see: Pommier, A.; Pons, J. M. Synthesis 1993, 441-459
10. Yang, H. W.; Romo, D. Tetrahedron 1999, 55, 6403-6434
11. Drent, E.; Kragtwijk, E. Eur. Pat. Appl. 577206, 1994; Chem. Abstr. 1994, 120, 191517c.
12. Lee, J. T.; Thomas, P. J.; Alper, H. J. Org. Chem. 2001, 66, 5424-5426
13. Heck, R. F. J. Am. Chem. Soc. 1963, 85, 1460-1463
14. Kramer, J. W.; Lobkovsky, E. B.; Coates, G. W. Org. Lett. 2006, 8, 3709-3712
15. Schmidt, J. A. R.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2005, 127, 11426-11435
16. Schmidt, J. A. R.; Mahadevan, V.; Getzler, Y. D. Y. L.; Coates, G. W. Org. Lett. 2004, 6, 373-376
17. Mahadevan, V.; Getzler, Y. D. Y. L.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781-2784
18. Getzler, Y. D. Y. L.; Mahadevan, V.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1174-1175
19. Molnar, F.; Luinstra, G. A.; Allmendinger, M.; Rieger, B. Chem.-Eur. J. 2003, 9, 1273-1280
20. Allmendinger, M.; Eberhardt, R.; Luinstra, G. A.; Molnar, F.; Rieger, B. Z. Anorg. Allg. Chem. 2003, 629, 1347-1352
21. Sisak, A.; Ungváry, F.; Markó, L. Organometallics 1983, 2, 1244-1246
22. Sisak, A.; Markó, L. J. Organomet. Chem. 1987, 330, 201-206
23. Fachinetti, G.; Fochi, G.; Funaioli, T. J. Organomet. Chem. 1986, 301, 91-97
24. Tasi, M.; Sisak, A.; Ungváry, F.; Pályi, G. Monatsh. Chem. 1985, 116, 1103-1105
25. Absi-Halabi, M.; Atwood, J. D; Forbus, N. P.; Brown, T. L. J. Am. Chem. Soc. 1980, 102, 6248-6254
26. Braterman, P. S.; Walker, B. S.; Robertson, T. H. J. Chem. Soc., Chem. Commun. 1977, 651-652
27. Fachinetti, G.; Funaioli, T.; Marcucci, M. J. Organomet. Chem. 1988, 353, 393-404
28. Braterman, P. S.; Leslie, A. E. J. Organomet. Chem. 1981, 214, C45-C49
29. Akula, R.; Galligan, M. J.; Ibrahim, H. Chem. Commun. 2009, 6991-6993
30. Akula, R.; Galligan, M. J.; Ibrahim, H. Synthesis 2011, 347-351
31. Chen, P.; Malcolm, H. C.; Gallucci, J. C.; Zhang, X.; Zhou, Z. Inorg. Chem. 2005, 44, 2588-2595
32. Both, a synthesized and a purchased sample from Strem Chemicals of (TPP)CrCl gave complete conversion to the product at a loading of 1000:1.
33. Bunnage, M. E.; Davies, S. G.; Roberts, P. M.; Smith, A. D.; Withey, J. M. Org. Biomol. Chem. 2004, 2, 2763-2776
34. Yokota, Y.; Cortez, G. S.; Romo, D. Tetrahedron 2002, 58, 7075-7080
35. For detailed mechanistic studies with aluminum complex 3a, see: Church, T. L.; Getzler, Y. D. Y. L.; Coates, G. W. J. Am. Chem. Soc. 2006, 128, 10125-10133