Ni(O)/ZnCl2-promoted coupling of enones and enynes. Domino process via formation of three C-C bonds and cleavage of one C-C bond

Journal of the American Chemical Society

Volumn 124, Issue 41, 2002, Pages 12060-12061

  Ikeda, Shin ichi ^a   Miyashita, Hitoshi ^a   Taniguchi, Masami ^a   Kondo, Hiroko ^a   Okano, Masaki ^a   Sato, Yoshiro ^a   Odashima, Kazunori ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CARBON; METAL COMPLEX; NICKEL CHLORIDE; ORGANOMETALLIC COMPOUND; ZINC CHLORIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERISM; SYNTHESIS;

EID: 0037120880     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0202863     Document Type: Article

References (28)

1. (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York, 1992.
2. (b) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York, 1994; p 79.
3. (a) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
4. (b) Bunce, R. A. Tetrahedron 1995, 51, 13103.
5. (c) Tietze, L. F. Chem. Rev. 1996, 96, 115.
6. (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
7. (b) Negishi, E. Pure Appl. Chem. 1992, 64, 323.
8. (c) Overman, L. E.; Abelman, M. M.; Kucera, D. J.; Tran, V. D.; Ricca, D. J. Pure Appl. Chem. 1992, 64, 1813.
9. (d) Grigg, R. J. Heterocycl. Chem. 1994, 31, 631.
10. (e) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
11. (f) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
12. (g) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
13. (h) Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65.
14. (i) de Meijere, A.; Brase, S. J. Organomet. Chem. 1999, 576, 88.
15. (a) Ikeda, S. Acc. Chem. Res. 2000, 33, 511. Ikeda, S. J. Synth. Org. Chem. Jpn. 2001, 59, 960. For related works, see: (b) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
16. (a) Ikeda, S. Acc. Chem. Res. 2000, 33, 511. Ikeda, S. J. Synth. Org. Chem. Jpn. 2001, 59, 960. For related works, see: (b) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
17. (a) Ikeda, S. Acc. Chem. Res. 2000, 33, 511. Ikeda, S. J. Synth. Org. Chem. Jpn. 2001, 59, 960. For related works, see: (b) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
18. Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370.
19. García-Gómez, G.; Moretó, J. M. Chem.-Eur. J. 2001, 7, 1503.
20. For an example of [2 + 2 + 2] cycloaddition of alkynyl enones with activated alkenes via nickellacycle, see: Seo, J.; Chui, H. M. P.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 476.
21. In the Mizoroki-Heck reaction, a variety of bases can promote the regeneration of Pd(0) from Pd(II). See ref 3.
22. Negishi and co-workers reported processes via ii-iv in the Pd-catalyzed arylation and alkenylation of enynes, see: Owczarczyk, Z.; Lamaty, F.; Vawter, E. J.; Negishi, E. J. Am. Chem. Soc. 1992, 114, 10091.
23. Regarding the Ni(0)-mediated (not catalytic) intramolecular cyclization of precursors with tethered vinyl bromides and alkenes, Delgado and co-workers cited ref 9 above, see: Solé, D.; Cancho, Y.; Llebaria, A.; Moretó, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133. However, they did not describe in their paper whether the reaction proceeded with an inversion or retention of the alkene configuration.
24. 11b These results suggest that the rapid addition-elimination of the nickel hydride species between III and V is present. In a similar manner as above, the presence of the rapid equilibrium between 6 and 8 is not rule out. (a) Pinke, P. A.; Miller, R. G. J. Am. Chem. Soc. 1974, 96, 4221. (b) Pinke, P. A.; Stauffer, R. D.: Miller, R. G. J. Am. Chem. Soc. 1974, 96, 4229.
25. 11b These results suggest that the rapid addition-elimination of the nickel hydride species between III and V is present. In a similar manner as above, the presence of the rapid equilibrium between 6 and 8 is not rule out. (a) Pinke, P. A.; Miller, R. G. J. Am. Chem. Soc. 1974, 96, 4221. (b) Pinke, P. A.; Stauffer, R. D.: Miller, R. G. J. Am. Chem. Soc. 1974, 96, 4229.
26. 12b (a) Howden, M. E. H.; Maerker, A.; Burdon, J.; Roberts, J. D. J. Am. Chem. Soc. 1966, 88, 1732. (b) Miller, R. G.; Pinke, P. A.; Stauffer, R. D.; Golden, H. J.; Baker, D. J. J. Am. Chem. Soc. 1974, 96, 4211.
27. 12b (a) Howden, M. E. H.; Maerker, A.; Burdon, J.; Roberts, J. D. J. Am. Chem. Soc. 1966, 88, 1732. (b) Miller, R. G.; Pinke, P. A.; Stauffer, R. D.; Golden, H. J.; Baker, D. J. J. Am. Chem. Soc. 1974, 96, 4211.
28. Huggins, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 3002.