Nickel-catalyzed cycloaddition of alkynes and isocyanates

Journal of the American Chemical Society

Volumn 126, Issue 37, 2004, Pages 11438-11439

  Duong, Hung A ^a   Cross, Michael J ^a   Louie, Janis ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; NICKEL;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; CYCLOADDITION; REACTION ANALYSIS; ROOM TEMPERATURE; SUBSTITUTION REACTION;

EID: 4544240649     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046477i     Document Type: Article

References (23)

1. (a) Varela, S. A.; Saa, C. Chem. Rev. 2003, 103, 3787.
2. (b) Wolkenberg, S. E.; Boger, D. L. J. Org. Chem. 2002, 67, 7361.
3. (c) Baxendale, I. R.; Ley, S. V.; Piutti, C. Angew. Chem., Int. Ed. 2002, 41, 2194.
4. (d) Cai, P.; Smith, D.; Cunningham, B.; Brown-Shimer, S.; Katz, B.; Pearce, C.; Venables, D.; Houck, D. J. Nat. Prod. 1999, 62, 397.
5. (e) Grotjahn, D. B. Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier Science Ltd: Oxford, 1995; Vol. 12, pp 741-770.
6. (f) Shore, N. E. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press Ltd: Oxford, 1991; Vol. 5, pp 1129-1162.
7. (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786.
8. (b) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333.
9. Yamamoto, Y.; Takagishi, H.; Itoh, K. Org. Lett. 2001, 3, 2117.
10. (a) Hoberg, H.; Oster, B. W. Synthesis 1982, 324.
11. (b) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35.
12. (c) Hoberg, H.; Oster, W. J. Organomet. Chem. 1983, 252, 359.
13. Takahashi, T.; Tsai, F. Y.; Li, Y.; Wang, H.; Kondo, Y.; Yamanaka, M.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 5059.
14. For examples of the use NHCs as ligands in various catalytic reactions, see: (a) Kuhl, S.; Schneider, R.; Fort, Y. Organometallics 2003, 22, 4184.
15. (b) Kuhl, S.; Schneider, R.; Fort, Y. Adv. Synth. Catal. 2003, 345, 341.
16. (c) McGuinness, D. S.; Mueller, W.; Wasserscheid, P.; Cavell, K. J.; Skelton, B. W.; White, A. H.; Englert, U. Organometallics 2002, 21, 175.
17. (d) Sato, Y.; Sawaki, R.; Mori, M. Organometallics 2001, 20, 5510.
18. Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N. J. Am. Chem. Soc. 2002, 124, 15188.
19. ICy = 1,3-dicyclohexylimidazol-2-ylidene; IAd = 1,3-diadamantylimidazol- 2-ylidene; ItBu = 1,3-di-tert-butylimidazol-2-ylidene; IMes = 1,3-bis-(2,4,6-trimethylphenyl)imidazol-2-ylidene; IPr = 1,3-bis-(2,6- diisopropylphenyl)imidazol-2-ylidene; SIPr = 1,3-bis-(2,6-diisopropylphenyl) imidazolin-2-ylidene.
20. (a) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
21. (b) Tsuda, T.; Morikawa, S.; Sumiya, R.; Saegusa, T. J. Org. Chem. 1988, 53, 3140.
22. In the reaction shown in eq 1, an arene product was identified to be 5-(2,2-bis-methoxycarbonyl-hex-4-ynyl)-4,6,7-trimethyl-indan-2,2-dicarboxylic acid dimethyl ester 4. (diagram presented)
23. 2 and SIPr are allowed to stir for 6 h prior to the cycloaddition reaction.