Nickel(0)-catalyzed [2 + 2 + 2 + 2] cycloadditions of terminal diynes for the synthesis of substituted cyclooctatetraenes

Journal of the American Chemical Society

Volumn 129, Issue 44, 2007, Pages 13402-13403

  Wender, Paul A ^a   Christy, Justin P ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; CYCLOOCTATETRAENE DERIVATIVE; NICKEL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLOADDITION; REACTION ANALYSIS; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; DIYNES; HYDROCARBONS, CYCLIC; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 35948930324     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0763044     Document Type: Article

References (35)

1. For reviews on the properties of COTs, see: (a) Klarner, F. Angew. Chem., Int. Ed. 2001, 40, 3877-3981.
2. (b) Spitler, E. L.; Johnson, C. A.; Haley, M. M. Chem. Rev. 2006, 106, 5344-5386.
3. (c) Paquette, L. A. Acc. Chem. Res. 1993, 26, 57-62 and references therein.
4. For a review on COTs being used as ligands for lanthanides, see: Hou, Z.; Wakatsuki Y. Sci. Syn. 2003, 2, 849-942 and references therein.
5. Wilke, G. Pure Appl. Chem. 1978, 50, 677-690.
6. Lu, P.; Hong, H.; Cai, G.; Djurovich, P.; Weber, W. P.; Thimpson, M. E. J. Am. Chem. Soc. 2000, 122, 7480-7486.
7. For examples, see: (a) Davis, R. E.; Dodds, T. A.; Hseu, T. H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7563.
8. (b) Rigby, J. H.; Scribner, S.; Heeg, M. J. Tetrahedron Lett. 1995, 36, 8569-8572.
9. (c) Achard, M.; Masrin, M.; Tenaglia, A.; Buono, G. J. Org. Chem. 2006, 71, 2907-2910.
10. For examples, see: (a) Cope, A. C.; Nelson, N. A.; Smith, D. S. J. Am. Chem. Soc. 1954, 76, 1100-1104 and references therein,
11. (b) Bianchi, Giorgio, Gandolfi, R.; Gruenanger, P. Tetrahedron 1970, 26, 5113-5122.
12. Scherman, O. A.; Rutenberg, I. M.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 8515-8522 and references therein.
13. Marsella, M. J.; Reid, R. J. Macromotecules 1999, 32, 5982-5984.
14. Gekki, S. P.; Talawar, T.; Mukundan, T.; Kurian, E. M. J. Hazard. Mater. 2006, 134, 36-40.
15. (a) Kelebekli, L.; Kara, Y.; Balci, M. Carbohydr. Res. 2005, 12, 1940-1948.
16. (b) Kelebekli, L.; Celik, M.; Sahin, E.; Kara, Y.; Balci, M. Tetrahedron Lett. 2006, 47, 7031-7035.
17. Ernest, I. Angew. Chem., Int. Ed. Engl. 1976, 15, 207-214 and references therein.
18. Willstatter, R.; Waser, W. Ber. Dtsch. Chem. Ges. 1911, 44, 3423-3445.
19. For recent examples of cyclooctatetraenes synthesis not from alkyne tetramerization, see: (a) Lawrie, C. J.; Gable, K. P.; Carpenter, B. K. Organometallics 1989, 8, 2274-2276.
20. (b) Rigby, J. H.; Warshakoon, N. C. Tetrahedron 1997, 38, 2049-2052.
21. (c) Yamamoto, Y.; Ohno, T.; Itoh, K. Chem. Eur. J. 2002, 8, 4734-4741.
22. (d) Chen, C.; Xi, C.; Lai, C.; Wang, R.; Hong, X. Eur. J. Org. Chem. 2004, 3, 647-650.
23. (e) Wang, C.; Yuan, J.; Li, G.; Wang, Z.; Zhang, S.; Xi, Z. J. Am. Chem. Soc. 2006, 128, 4564-4565.
24. Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron 2006, 62, 7505-7511 and references therein.
25. Reppe, W.; Schlichting, O.; Klager, K.; Toepel, T. Justus Liebigs Ann. Chem. 1948, 560, 1-92.
26. For examples of tetramerizations of alkynes other than acetylene, see: (a) Cope A. C.; Pike, R. M. J. Am. Chem. Soc. 1953, 75, 3220-3223 and references therein,
27. (b) Leto, J. R.; Leto, M. F. J. Am. Chem. Soc. 1961, 83, 2944-2951.
28. (c) Chini, P.; Palladino, N.; Santambrogio, A. J. Chem. Soc. C 1967, 836-840.
29. (d) Boussie, T. R.; Streitwieser, A. J. Org. Chem. 1993, 58, 2377-2380.
30. Diercks, R.; tom Dieck, H. Chem. Ber. 1985, 188, 428-435 and references therein.
31. For other examples of 1,6-diynes forming COTs, see: (a) Wagner, F.; Meier, H. Tetrahedron 1974, 30, 773-780.
32. (b) Chiusoli, G. P.; Pallini, L.; Terenghi, M. G. Transition Met. Chem. 1985, 10, 350-351.
33. (a) For a review, see: Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915.
34. (b) For an example of diynes reacting with other π-components, see: Tekavec, T. N.; Zuo, G.; Simon K.; Louie, J. J. Org. Chem. 2006, 71, 5834-5836.
35. 2) results in a more reproducible reduction of the Ni(II) precatalyst.