Nickel(0)-Promoted Cyclization of Enynes with Isocyanides: A New Route to Polycyclic Cyclopentenone Skeletons

Journal of the American Chemical Society

Volumn 110, Issue 4, 1988, Pages 1286-1288

  Tamao, Kohei ^a   Kobayashi, Kenji ^a   Ito, Yoshihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001353739     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00212a045     Document Type: Letter

References (9)

1. Reviews: (a) Zirconium: Negishi, E.-I. Acc. Chem. Res. 1987, 20, 65. (b) Cobalt: Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207. (c) Nickel and palladium: Chiusoli, G. P. J. Organomet. Chem. 1986, 300, 57.
2. Representative examples are as follows. Titanium: (a) McDermott, J. X.; Wilson, M. E.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 6529. (b) Grubbs, R. H.; Miyashita, A. J. Chem. Soc., Chem. Commun. 1977, 864. (c) Parshall, G. W.; Nugent, W. A.; Chan, D. M.-T.; Tam, W. Pure Appl. Chem. 1985, 57, 1809. Zirconium: (d) Manriquez, J. M.; McAlister, D. R.; Sanner, R. D.; Bercaw, J. E. J. Am. Chem. Soc. 1978, 100, 2716. (e) Yasuda, H.; Nagasuna, K.; Akita, M.; Lee, K.; Nakamura, A. Organometallics 1984, 3, 1470. (f) Negishi, E.-I.; Holmes, S. J.; Tour, J. M.; Miller, J. A. J. Am. Chem. Soc. 1985, 107, 2568. (g) Negishi, E.-I.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829. (h) Buchwald, S. L.; Watson, B.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544. Cobalt: (i) Billington, D. C.; Pauson, P. L. Organometallics 1982, 1, 1560. (j) Billington, D. C. Tetrahedron Lett. 1983, 24, 2905. (k) Shore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436. (l) Exon, C.; Magnus, P. J. Am. Chem. Soc. 1983, 105, 2477. (m) Billington, D. C.; Willison, D. Tetrahedron Lett. 1984, 25, 4041. (n) Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851. (o) Smit, W. A.; Gybin, A. S.; Shashkov, E. D.; Strychkov, Y. T.; Kyz'mina, L. G.; Mikaelian, G. S.; Caple, R.; Swanson, E. D. Tetrahedon Lett. 1986, 27, 1241. (p) Simanian, S. O.; Smit, W. A.; Gybin, A. S.; Shashkov, A. S.; Mikaelian, G. S.; Tarasov, V. A.; Ibragimov, I. I.; Caple, R.; Froen, D. E. Tetrahedron Lett. 1986, 27, 1245. (q) Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128. Nickel: (r) Grubbs, R. H.; Miyashita, A.; Liu, M.; Burk, P. J. Am. Chem. Soc. 1978, 100, 2418.
3. Nickel-isocyanide complexes have been extensively studied by Otsuka and his co-workers. (a) Otsuka, S.; Nakamura, A.; Tatsuno, Y. J. Am. Chem. Soc. 1969, 91, 6994. (b) Otsuka, S.; Yoshida, T.; Tatsuno, Y. J. Am. Chem. Soc. 1971, 93, 6462. (c) Otsuka, S.; Nakamura, A.; Yoshida, T.; Naruto, M.; Ataka, K. J. Am. Chem. Soc. 1973, 95, 3180.
4. No reaction occurred under CO atmosphere In the course of our present study, Trost reported a 1, 3-diene synthesis from enynes catalyzed by nickel-chromium systems: Trost, B. M.; Tour, M. J. Am. Chem. Soc. 1987, 109, 5268.
5. Formation of nickelacyclopentanes2r and nickelacyclopentadienes from nickel(0) complexes with ethylene and acetylenes, respectively, has been reported. Eisch, J. J.; Damasevitz, G. A. J. Organomet. Chem. 1975, 96, C19.
6. A closely related reaction is the formation of cyclic imines from bis(π-allyl)nickels and an isocyanide: Baker, R.; Cookson, R. C.; Vinson, J. R. J. Chem. Soc., Chem. Commun. 1974, 515. Baker, R.; Copeland, A. H. Tetrahedron Lett, 1976, 4535.
7. 3b Dickson, R. S.; Ibers, J. A. J. Organomet. Chem. 1972, 36, 191. It has also been reported that the reaction of tetrakis(isocyanide)nickel(0) with diphenylacetylene affords diiminocyclobutenes: Suzuki, Y.; Takizawa, T. J. Chem. Soc., Chem. Commun. 1972, 837.
8. Note Added in Proof. Eisch and his co-workers reported several years ago nickel(0)-mediated reactions of diphenylacetylene with trimethylsilyl isocyanide and proposed an iminonickelacyclobutene intermediate: Eisch, J. J.; Aradi, A. A.; Han, K. I. Tetrahedron Lett. 1983, 24, 2073.
9. Tamao, K.; Kumada, M. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; John Wiley: Chichester, 1987; Vol. 4, pp 819–887. Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 613–797.