Synthesis of biaryls using nickel-catalyzed [2+2+2] cocyclization

Tetrahedron Letters

Volumn 40, Issue 28, 1999, Pages 5231-5234

  Sato, Yoshihiro ^a   Ohashi, Kenji ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

2+2+2 Cocyclization; Biaryl; Cotrimerization; Cycloaddition; Nickel catalyst

Indexed keywords

ACETYLENE; CYCLOPENTADIENE DERIVATIVE; NICKEL;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; CYCLIZATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033538606     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00945-4     Document Type: Article

References (13)

1. For [2+2+2] cycloaddition of alkenes and alkynes; (a) Schore, N. E. In Comprehensive Organic Synthesis: Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 9.4.
2. (b) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995: Vol. 12, Chapter 7.3.
3. (c) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
4. (a) Bhatarah, P.; Smith, E. H. J. Chem. Soc. Perkin Trans. 1 1990, 2603.
5. (b) Bhatarah, P.; Smith. E. H. Chem. Commun. 1991. 277.
6. (c) Bhatarah, P.; Smith, E. H. J. Chem. Soc. Perkin Trans. 1 1992, 2169.
7. (a) Sato, Y.; Nishimata, T.; Mori, M. J. Org. Chem. 1994, 59, 6133.
8. (b) Sato, Y.; Nishimata, T.; Mori. M. Heterocycles 1997, 44, 443.
9. For recent examples of Ni-catalyzed [2+2+2] cocyclization of alkenes and alkynes: (a) Ikeda, S.; Watanabe, H.; Sato, Y. J. Org. Chem. 1998, 63, 7026 and references cited therein,
10. (b) Seo, J.; Chui, H. M. P.; Heeg, M. J.: Montgomery, J. J. Am. Chem. Soc. 1999, 121, 476.
11. For the synthesis of biaryls via aryl-aryl coupling reactions, see: Knight, D. W. In Comprehensive Organic Synthesis; Trost. B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 2.3.
12. (a) For Pd-catalyzed cyclotrimerization of 1,3-diynes; Takeda, A.; Ohno, A.; Kadota, I.; Gevorgyan, V.: Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 4547.
13. (b) Very recently, Co(I)-catalyzed [2+2+2] cycloadditions of diyne 3 with two molecules of 5- hexynenitrile were reported, in which 3,3'-susbtituted 2,2'-bipyridine derivatives were obtained. See: Varela. J. A.; Castedo, L.; Saá, C. J. Am. Chem. Soc. 1998, 120, 12147.