Microwave accelerated Glaser–Hay macrocyclizations at high concentrations

Chemical Communications

Volumn 48, Issue 51, 2012, Pages 6420-6422

  Bédard, Anne Catherine ^a   Collins, Shawn K ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; MICROWAVE IRRADIATION; TEMPERATURE SENSITIVITY;

EID: 84862214523     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc32464d     Document Type: Article

References (31)

1. J. C. Roxburgh, Tetrahedron, 1995, 51, 9767.
2. E. M. Driggers, S. P. Hale, J. Lee, N. K. Terrett, Nat. Rev. Drug Discovery, 2008, 7, 608.
3. E. Marsault, M. L. Peterson, J. Med. Chem., 2011, 54, 1961.
4. H. Matsuda, S. Watanabe, K. Yamamoto, Chem. Biodiversity, 2004, 1, 1985.
5. G. Rueedi, M. Nagel, H.-J. Hansen, Org. Lett., 2004, 6, 2989.
6. C. Fehr, J. Galindo, O. Etter, W. Thommen, Angew. Chem., Int. Ed., 2002, 41, 4523.
7. P. Bolduc, A. Jacques, S. K. Collins, J. Am. Chem. Soc., 2010, 132, 12790.
8. C. J. White, A. K. Yudin, Nat. Chem., 2011, 3, 509.
9. V. Farina, C. Shu, X. Zeng, X. Wei, Z. Han, N. K. Yee, C. H. Senanayake, Org. Process Res. Dev., 2009, 13, 250.
10. L. R. Odell and M. Larhed, in Handbook of Green Chemistry, ed. P. T. Anastas and R. H. Crabtree, 2009, vol.1, pp. 79.
11. C. O. Kappe, D. Dallinger, Nat. Rev. Drug Discovery, 2006, 5, 51.
12. A. Lampa, A. E. Ehrenberg, A. Vema, E. Aakerblom, G. Lindeberg, U. H. Danielson, A. Karlen, A. Sandstroem, Bioorg. Med. Chem., 2011, 19, 4917.
13. S. N. Khan, A. Kim, R. H. Grubbs, Y.-U. Kwon, Org. Lett., 2011, 13, 1582.
14. D. Obermayer, T. N. Glasnov, C. O. Kappe, J. Org. Chem., 2011, 76, 6657.
15. M. Damm, T. N. Glasnov, C. O. Kappe, Org. Process Res. Dev., 2010, 14, 215.
16. A.-C. Bédard, S. K. Collins, J. Am. Chem. Soc., 2011, 133, 19976.
17. G. Stavber, Aust. J. Chem., 2010, 63, 849.
18. U. Hasegawa, A. J. van der Vlies, E. Simeoni, C. Wandrey, J. A. Hubbell, J. Am. Chem. Soc., 2010, 132, 18273.
19. W.-F. Dong, A. Kishimura, Y. Anraku, S. Chuanoi, K. Kataoka, J. Am. Chem. Soc., 2009, 131, 3805.
20. W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem., Int. Ed. Engl., 1993, 32, 1524.
21. I. T. Horvath, J. Rabai, Science, 1994, 266, 72.
22. R. Correa da Costa, J. A. Gladysz, Adv. Synth. Catal., 2007, 349, 243.
23. D. P. Curran, S. Hadida, S.-Y. Kim, Z. Luo, J. Am. Chem. Soc., 1999, 121, 6607.
24. A. S. William, Synthesis, 1999, 1707.
25. S. E. Wolkenberg, W. D. Shipe, C. W. Lindsley, J. P. Guare, J. M. Pawluczyk, Curr. Opin. Drug Discovery & Development, 2005, 8, 701.
26. M. G. Organ, P. R. Hanson, A. Rolfe, T. B. Samarakoon, F. Ullah, J. Flow Chem., 2011, 1, 32.
27. G. Shore, W.-J. Yoo, C.-J. Li, M. G. Organ, Chem.-Eur. J., 2010, 16, 126.
28. C. Conner, G. A. Tompsett, J. Phys. Chem. B, 2008, 112, 2110.
29. Acetylene Chemistry: Chemistry, Biology, and Material Science, ed. F. Diederich, P. J. Stang and R. R. Tykwinski, Wiley-VCH, Weinheim, Germany, 2005
30. A. S. Hay, J. Org. Chem., 1960, 25, 1275.
31. A. S. Hay, J. Org. Chem., 1962, 27, 3320.