1,3-Bis(N,N-dialkylamino)imidazolin-2-ylidenes: Synthesis and reactivity of a new family of stable N-heterocyclic carbenes

Journal of the American Chemical Society

Volumn 126, Issue 41, 2004, Pages 13242-13243

  Alcarazo, Manuel ^a   Roseblade, Stephen J ^a   Alonso, Emma ^a   Fernández, Rosario ^b   Alvarez, Eleuterio ^a   Lahoz, Fernando J ^c   Lassaletta, José M ^a  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b UNIVERSITY OF SEVILLE   (Spain)

^c Universidad de Zaragoza Consejo Superior de Investigaciones Científicas   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; IMIDAZOLIN 2 YLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHIRALITY; DIELS ALDER REACTION; ENANTIOSELECTIVITY; LIGAND BINDING; SYNTHESIS; X RAY DIFFRACTION;

EID: 6044232045     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0471119     Document Type: Article

References (21)

1. Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
2. (a) Bourissou, D.; Guerret, O.; Gablaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
3. (b) Alder, R. W. In Carbene Chemistry: From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Marcel Dekker Inc.: New York, 2002; Chapter 5, pp 153-176.
4. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
5. Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951-961.
6. Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2607-2609.
7. Arduengo, A. J.; Davidson, F.; Dias, H. V. R.; Goerlich, J. R.; Khasnis, D.; Marshall, W. J.; Prakasha, T. K. J. Am. Chem. Soc. 1997, 119, 12742-12749.
8. Arduengo, A. J.; Dias, H. V. R.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530-5534.
9. Arduengo, A. J.; Goerlich, J. R.; Marshall, W. J. J. Am. Chem. Soc. 1995, 117, 11027-11028.
10. Alder, R. W.; Blake, M. E.; Borlotti, C.; Bufali, S.; Butts, C. P.; Linehan, E.; Oliva, J. M.; Orpen, A. G.; Quayle, M. Chem. Commun. 1999, 241-242.
11. Alder, R. W.; Allen, P. R.; Murray, M.; Orpen, A. G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1121-1123.
12. Enders, D.; Breuer, F.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Bride, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021-1023.
13. Hahn, F. E.; Wittenbecher, L.; Boese, R.; Bläser, D. Chem. Eur. J. 1999, 5, 1931-1935.
14. Alcarazo, M.; Fernández, R.; Lassaletta, J. M. Chem. Commun. 2004, 298-299.
15. The lack of interaction of amidinium system with N-ferrocenyl substituents has also been reported: Bildstein, B.; Malaun, M.; Kopacka H.; Wurts, K.; Mitterböck, M.; Ongania, K.-H.; Opromolla, G.; Zanello, P. Organometallics 1999, 18, 4325-4336. See also ref 7.
16. Arduengo, A. J.; Calabrese, J. C.; Davidson, F.; Dias, H. V. R.; Goerlich, J. R.; Krafczyk, R.; Marshall, W. J.; Tamm, M.; Schmutzler Helv. Chim. Acta 1999, 82, 2348-2364.
17. Köcher, C.; Herrmann, W. A. J. Organomet. Chem. 1997, 532, 261-265.
18. Denk, K.; Sirsh, P.; Herrmann, W. A. J. Organomet. Chem. 2002, 649, 219-224.
19. (a) Mayr, M.; Wurst, K.; Ongania, K.-H.; Buchmeiser, M. R. Chem. Eur. J. 2004, 10, 1256-1266.
20. (b) Bazinet, P.; Yap, G. P. A.; Richeson, D. S. J. Am. Chem. Soc. 2003, 125, 13314-13315.
21. Enders, D.; Meiers, M. Synthesis 2002, 2542-2559.