Synthesis of 2-haloalkylpyridines via Cp*RuCl-catalyzed cycloaddition of 1,6-diynes with α-halonitriles. Unusual halide effect in catalytic cyclocotrimerization

Advanced Synthesis and Catalysis

Volumn 347, Issue 15, 2005, Pages 1913-1916

  Yamamoto, Yoshihiko ^a   Kinpara, Keisuke ^a   Nishiyama, Hisao ^a   Itoh, Kenji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Alkynes; Cyanides; Cyclotrimerization; Pyridines; Ruthenium

Indexed keywords

EID: 29144506116     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505193     Document Type: Article

References (24)

1. a) N. E. Shore, in: Comprehensive Organic Synthesis, Vol. 5, (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, pp. 1129-1162;
2. b) D. B. Grotjahn, in: Comprehensive Organometallic Chemistry II, Vol. 12, (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson, L. S. Hegedus), Pergamon, Oxford, 1995, pp. 741-770;
3. c) H. Bönnemann, W. Brijoux, in: Transition Metals for Organic Synthesis, Vol. 1, (Eds.: M. Beller, C. Bolm), Wiley, Weinheim, 1998, pp.114-135;
4. d) J. A. Varela, C. Saá, Chem. Rev. 2003, 103, 3787-3801.
5. a) Y. Wakatsuki, H. Yamazaki, J. Chem. Soc. Chem. Commun. 1973, 280;
6. b) D. Suzuki, R. Tanaka, H. Urabe, F. Sato, J. Am. Chem. Soc. 2002, 124, 3518-3519;
7. c) T. Takahashi, F.-Y. Tsai, Y. Li, H. Wang, Y. Kondo, M. Yamanaka, K. Nakajima, M. Kotora, J. Am. Chem. Soc. 2002, 124, 5059-5067.
8. a) A. Gutnov, B. Heller, C. Fischer, H.-J. Drexler, A. Spannenberg, B. Sundermann, C. Sundermann, Angew. Chem. 2004, 116, 3883-3886;
9. Angew. Chem. Int. Ed. 2004, 43, 3795-3797;
10. b) M. M. McCormick, H. A. Duong, G. Zuo, J. Louie, J. Am. Chem. Soc. 2005, 127, 5030-5031.
11. a) L. V. R. Boñaga, H.-C. Zhang, A. F. Moretto, H. Ye, D. A. Gauthier, J. Li, G. C. Leo, B. E. Maryanoff, J. Am. Chem. Soc. 2005, 127, 3473-3485;
12. b) L. V. R. Boñaga, H.-C. Zhang, B. E. Maryanoff, Chem. Commun. 2004, 2394-2395.
13. Y. Yamamoto, K. Kinpara, T. Saigoku, H. Takagishi, S. Okuda, H. Nishiyama, K. Itoh, J. Am. Chem. Soc. 2005, 127, 605-613.
14. Y. Yamamoto, R. Ogawa, K. Itoh, J. Am. Chem. Soc. 2001, 123, 6189-6190.
15. The cationic ruthenium-catalyzed cycloaddition of chloroacetonitrile was reported but the yield was moderate: J. A. Varela, L. Castedo, C. Saá, J. Org. Chem. 2003, 68, 8595-8598.
16. T. K. Hayes, R. Villani, S. M. Weinreb, J. Am. Chem. Soc. 1988, 110, 5533-5543.
17. a) Y. Yamamoto, T. Arakawa, R. Ogawa, K. Itoh, J. Am. Chem. Soc. 2003, 125, 12143;
18. b) K. Kirchner, M. J. Calhorda, R. Schmid, L. F. Veiros, J. Am. Chem. Soc. 2003, 125, 11721-11729;
19. c) R. Schmid, K. Kirchner, J. Org. Chem. 2003, 68, 8339-8344.
20. Y. Yamamoto, K. Kinpara, T. Saigoku, K. Itoh, Org. Biomol. Chem. 2004, 2, 1287-1294.
21. K. Fagnou, M. Lautens, Angew. Chem. 2002, 114, 26-49;
22. Angew. Chem. Int. Ed. 2002, 41, 26-47.
23. a) J. A. Orvik, (Dow Chemical Co., USA), European Patent Appl. 243853, 1987;
24. b) T. W. Holmsen, N. H. Kurihara, P. A. Thomas, (Dow Chemical Co., USA), U. S. Patent 4,266,964, 1981.