[3+2]-Dipolar cycloaddition reactions of an N-heterocyclic carbene boryl azide

Organic Letters

Volumn 14, Issue 11, 2012, Pages 2690-2693

  Merling, Everett ^a   Lamm, Vladimir ^a   Geib, Steven J ^a   Lacôte, Emmanuel ^b,c   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^c SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84861797436     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300851m     Document Type: Article

References (41)

1. Curran, D. P.; Solovyev, A.; Makhlouf Brahmi, M.; Fensterbank, L.; Malacria, M.; Lacôte, E. Angew. Chem., Int. Ed. 2011, 50, 10294-10317
2. Wang, Y.; Robinson, G. H. Inorg. Chem. 2011, 50, 12326-12337
3. Makhouf Brahmi, M.; Monot, J.; Desage-El Murr, M.; Curran, D. P.; Fensterbank, L.; Lacôte, E.; Malacria, M. J. Org. Chem. 2010, 75, 6983-6985
4. Monot, J.; Makhlouf Brahmi, M.; Ueng, S.-H.; Robert, C.; Desage-El Murr, M.; Curran, D. P.; Malacria, M.; Fensterbank, L.; Lacôte, E. Org. Lett. 2009, 11, 4914-4917
5. Chu, Q.; Makhlouf Brahmi, M.; Solovyev, A.; Ueng, S.-H.; Curran, D. P.; Malacria, M.; Fensterbank, L.; Lacôte, E. Chem.-Eur. J. 2009, 15, 12937-12940
6. Ueng, S.-H.; Fensterbank, L.; Lacôte, E.; Malacria, M.; Curran, D. P. Org. Lett. 2010, 12, 3002-3005
7. Horn, M.; Mayr, H.; Lacôte, E.; Merling, E.; Deaner, J.; Wells, S.; McFadden, T.; Curran, D. P. Org. Lett. 2012, 14, 82-85
8. Pan, X.; Lacôte, E.; Lalevée, J.; Curran, D. P. J. Am. Chem. Soc. 2012, 134, 5669-5674
9. Lindsay, D. M.; McArthur, D. Chem. Commun. 2010, 46, 2474-2476
10. Tehfe, M.-A.; Makhlouf Brahmi, M.; Fouassier, J.-P.; Curran, D. P.; Malacria, M.; Fensterbank, L.; Lacôte, E.; Lalevée, J. Macromolecules 2010, 43, 2261-2267
11. Tehfe, M.-A.; Monot, J.; Makhlouf Brahmi, M.; Bonin-Dubarle, H.; Curran, D. P.; Malacria, M.; Fensterbank, L.; Lacôte, E.; Lalevée, J.; Fouassier, J.-P. Polym. Chem. 2011, 2, 625-631
12. Tehfe, M.-A.; Monot, J.; Malacria, M.; Fensterbank, L.; Fouassier, J.-P.; Curran, D. P.; Lacôte, E.; Lalevée, J. ACS Macro Lett. 2011, 1, 92-95
13. Wang, Y.; Quillian, B.; Wei, P.; Wannere, C. S.; Xie, Y.; King, R. B.; Schaefer, H. F.; Schleyer, P. v. R.; Robinson, G. H. J. Am. Chem. Soc. 2007, 129, 12412-12413
14. Wang, Y.; Quillian, B.; Wei, P.; Xie, Y. M.; Wannere, C. S.; King, R. B.; Schaefer, H. F.; Schleyer, P. v. R.; Robinson, G. H. J. Am. Chem. Soc. 2008, 130, 3298-3299
15. Monot, J.; Solovyev, A.; Bonin-Dubarle, H.; Derat, é.; Curran, D. P.; Robert, M.; Fensterbank, L.; Malacria, M.; Lacôte, E. Angew. Chem., Int. Ed. 2010, 49, 9166-9169
16. Braunschweig, H.; Chiu, C.-W.; Radacki, K.; Kupfer, T. Angew. Chem., Int. Ed. 2010, 49, 2041-2044
17. Jana, A.; Azhakar, R.; Tavčar, G.; Roesky, H. W.; Objartel, I.; Stalke, D. Eur. J. Inorg. Chem. 2011, 3686-3689
18. Wang, Y.; Xie, Y.; Abraham, M. Y.; Wei, P.; Schaefer, H. F.; Schleyer, P. v. R.; Robinson, G. H. Organometallics 2011, 30, 1303-1306
19. Bissinger, P.; Braunschweig, H.; Damme, A.; Dewhurst, R. D.; Kupfer, T.; Radacki, K.; Wagner, K. J. Am. Chem. Soc. 2011, 133, 19044-19047
20. McArthur, D.; Butts, C. P.; Lindsay, D. M. Chem. Commun. 2011, 47, 6650-6652
21. Solovyev, A.; Geib, S. J.; Lacôte, E.; Curran, D. P. Organometallics 2012, 31, 54-56
22. Curran, D. P.; Boussonnière, A.; Geib, S. J.; Lacôte, E. Angew. Chem., Int. Ed. 2012, 51, 1602-1605
23. Bissinger, P.; Braunschweig, H.; Kraft, K.; Kupfer, T. A Angew. Chem. Int. Ed. 2011, 50, 4704-4707
24. Solovyev, A.; Chu, Q.; Geib, S. J.; Fensterbank, L.; Malacria, M.; Lacôte, E.; Curran, D. P. J. Am. Chem. Soc. 2010, 132, 15072-15080
25. Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188-5240
26. Organic azides: Synthesis and applications; Bräse, S.; Banert, K., Eds.; Wiley: Chichester, 2010.
27. Lwowski, W. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 559-652.
28. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021
29. Sisido, K.; Nabika, K.; Isida, T.; Kozima, S. J. Organomet. Chem. 1971, 33, 337-346
30. Kozima, S.; Itano, T.; Mihara, N.; Sisido, K.; Isida, T. J. Organomet. Chem. 1972, 44, 117-126
31. Hitomi, T.; Kozima, S. J. Organomet. Chem. 1977, 127, 273-280
32. Pocar, D.; Ripamonti, M. C.; Stradi, R.; Trimarco, P. J. Heterocycl. Chem. 1977, 14, 173-181
33. Miller, N. E.; Chamberland, B. L.; Muetterties, E. L. Inorg. Chem. 1964, 3, 1064-1065
34. Skillern, K. R.; Kelly, H. C. Inorg. Chem. 1977, 16, 3000-3005
35. Bettinger, H. F.; Filthaus, M.; Neuhaus, P. Chem. Commun. 2009, 2186-2188
36. Bettinger, H. F.; Filthaus, M.; Bornemann, H.; Oppel, I. M. Angew. Chem., Int. Ed. 2008, 47, 4744-4747
37. Keicher, T.; Löbbecke, S. In Organic Azides: Synthesis and Applications; Bräse, S.; Banert, K., Eds.; Wiley: Chichester, 2010, pp 1-28.
38. Huang, C.-C.; Wu, F.-L.; Lo, Y. H.; Lai, W.-R.; Lin, C.-H. Acta Crystallogr., Sect. E 2010, 66, o1690
39. Ogawa, A.; Curran, D. P. J. Org. Chem. 1997, 62, 450-451
40. Maul, J. J.; Ostrowski, P. J.; Ublacker, G. A.; Linclau, B.; Curran, D. P. In Modern Solvents in Organic Synthesis; Knochel, P., Ed.; Topics in Current Chemistry; Springer-Verlag: Berlin, 1999; Vol. 206, pp 80-104.
41. Huisgen, W. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 1-176.