Preparation of NHC borane complexes by lewis base exchange with amine- and phosphine-boranes

Journal of Organic Chemistry

Volumn 75, Issue 20, 2010, Pages 6983-6985

  Brahmi, Malika Makhlouf ^a   Monot, Julien ^a,b   Desage El Murr, Marine ^a   Curran, Dennis P ^b   Fensterbank, Louis ^a   Lacôte, Emmanuel ^a   Malacria, Max ^a  

^a SORBONNE UNIVERSITÉ   (France)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE COMPLEXES; LEWIS BASE;

BORON; HYDRIDES; ORGANIC COMPOUNDS; PHOSPHORUS COMPOUNDS;

BORON COMPOUNDS;

AMINE; BORANE DERIVATIVE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; LEWIS BASE; PHOSPHINE;

ARTICLE; COMPLEX FORMATION; MOLECULAR STABILITY; STEREOSPECIFICITY;

AMINES; BORANES; HETEROCYCLIC COMPOUNDS; METHANE; MOLECULAR STRUCTURE; PHOSPHINES; STEREOISOMERISM;

EID: 77957921347     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101301d     Document Type: Article

References (32)

1. Kuhn, N.; Henke, G.; Kratz, T.; Kreutzberg, J.; Boese, R.; Maulitz, A. H. Chem. Ber. 1993, 126, 2041-2045
2. Wacker, A.; Pritzkow, H.; Siebert, W. Eur. J. Inorg. Chem. 1999, 789-793
3. Ramnial, T.; Jong, H.; McKenzie, I. D.; Jennings, M.; Clyburne, J. A. C. Chem. Commun. 2003, 1722-1723
4. Wang, Y.; Quillian, B.; Wei, P.; Wannere, C. S.; Xie, Y.; King, R. B.; Schaefer, H. F., III; Schleyer, P. v. R.; Robinson, G. H. J. Am. Chem. Soc. 2007, 129, 12412-12413
5. Yamaguchi, Y.; Kashiwabara, T.; Ogata, K.; Miura, Y.; Nakamura, Y.; Kobayashi, K.; Ito, T. Chem. Commun. 2004, 2160-2161
6. Holschumacher, D.; Banneberg, T.; Hrib, C. G.; Jones, P. G.; Tamm, M. Angew. Chem., Int. Ed. 2008, 47, 7428-7432
7. Chase, P. A.; Stephan, D. W. Angew. Chem., Int. Ed. 2008, 47, 7433-7337
8. Wood, T. K.; Piers, W. E.; Keay, B. A.; Parvez, M. Angew. Chem., Int. Ed. 2009, 48, 4009-4012
9. Braunschweig, H.; Chiu, C.-W.; Radacki, K.; Kupfer, T. Angew. Chem., Int. Ed. 2010, 49, 2041-2044
10. Zheng, X.; Herberich, G. E. Organometallics 2000, 19, 3751-3753
11. Matsumoto, T.; Gabbaï, F. P. Organometallics 2009, 28, 4252-4253
12. Lee, K.-s.; Zhugralin, A. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 7253-7255
13. Ueng, S.-H.; Makhlouf Brahmi, M.; Derat, E.; Fensterbank, L.; Lacôte, E.; Malacria, M.; Curran, D. P. J. Am. Chem. Soc. 2008, 130, 10082-10083
14. Ueng, S.-H.; Solovyev, A.; Yuan, X.; Geib, S.; Fensterbank, L.; Lacôte, E.; Malacria, M.; Newcomb, M.; Walton, J. C.; Curran, D. P. J. Am. Chem. Soc. 2009, 131, 11256-11262
15. 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
16. Lindsay, D. M.; McArthur, D. Chem. Commun. 2010, 46, 2474-2476
17. Walton, J. C.; Makhlouf Brahmi, M.; Fensterbank, L.; Lacôte, E.; Malacria, M.; Chu, Q.; Ueng, S.-H.; Solovyev, A.; Curran, D. P. J. Am. Chem. Soc. 2010, 132, 2350-2358
18. Ueng, S.-H.; Fensterbank, L.; Lacôte, E.; Malacria, M.; Curran, D. P. Org. Lett. 2010, 12, 3002-3005
19. Solovyev, A.; Ueng, S.-H.; Monot, J.; Fentserbank, L.; Malacria, M.; Lacôte, E.; Curran, D. P. Org. Lett. 2010, 12, 2998-3001
20. 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
21. 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 (21) 4914-4917
22. Nielsen, D. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. Inorg. Chem. Acta 2003, 352, 143-150
23. Cattoën, X.; Gornitzka, H.; Bourissou, D.; Bertrand, G. J. Am. Chem. Soc. 2004, 126, 1342-1343
24. Brisset, H.; Gourdel, Y.; Pellon, P.; Le Corre, M. Tetrahedron Lett. 1993, 34, 4523-4526
25. Carboni, B.; Carreaux, F. In Science of Synthesis, Organometallics: Boron Compounds; Kaufmann, D. E.; Matteson, D. S., Eds; Verlag: Stuttgart, Germany, 2004; Vol. 6, pp 455 - 484.
26. Gaumont, A. C.; Carboni, B. In Science of Synthesis, Organometallics: Boron Compounds; Kaufmann, D. E.; Matteson, D. S., Eds; Verlag: Stuttgart, 2004; Vol. 6, pp 485 - 512.
27. Arduengo, A. J., III; Krafczyk, R.; Schmutzler, R. Tetrahedron 1999, 55, 14523-14534
28. Lesley, M. J. G.; Woodward, A.; Taylor, N. J.; Marder, T. B. Chem. Mater. 1998, 10, 1355-1365
29. Singaram, B.; Cole, T. E.; Brown, H. C. Organometallics 1984, 3, 774-777
30. Hawthorne, M. F. J. Am. Chem. Soc. 1958, 80, 4291-4293
31. An alternative way to NHC boranes has been proposed by Braunschweig while this manuscript was under review. It involves carboxylate derivatives of NHCs as the NHC source, but uses borane-dimethyl sulfide as the boron source
32. See: Bissinger, P.; Braunschweig, H.; Kupfer, T.; Radacki, K. Organometallics 2010, 29, 3987-3990. This paper introduces NHC boranes as ligands for transition metals.