Preparation of pyridylethynyl benzonitriles

Chinese Journal of Organic Chemistry

Volumn 21, Issue 7, 2001, Pages 514-517

  Wang, Zhi Yong ^a   Li, Qian Rong ^a   Jiang, Chao ^a   Zhou, Cun Liu ^a   Guo, Qing Xiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Coupling reaction; Pd(0) catalysis; Pyridylethynyl benzonitrile compounds

Indexed keywords

EID: 0035652030     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. Micetich, R. G. The Chemistry of Heterocyclic Compounds, Eds. : Abramovitch, R. A. , Wiley, New York, 1974, Supplement Part 2, p. 14.
2. (a) Chambers, R. J. ; Manfat ,A. ; Cheng, J. B. ; Cohan, V. L. ; Damon, D. B. ; Duplantie, A. J. ; Hibbs, T. A. ; Jenkinson, T. H. ; Johnson, K. L. ; Kraus, K. G. ; Pettipher, E. R. ; Salter, E. D. ; Shirley, J. T. ; U mLand, J. P. Bioorg. Med. Chem. Lett. 1997, 7, 739.
3. (b) Boyd, E. C. ; Eaton, M. A. W. ; Warrellow, G. J. WO 9410118, 1994 [ Chem. Abstr. 1994, 122, 31544].
4. (b) Boyd, E. C. ; Eaton, M. A. W. ; Warrellow, G. J. WO 9410118, 1994 [ Chem. Abstr. 1994, 122, 31544].
5. (a) Maini, R. N. ; Elliot, M. J. ; Rennan, F. M. ; Feldmann, M. Clin. Exp. Immunol. 1995, 101, 207.
6. (b) Elliot, M. J. ; Maini, R. N. ; Feldmann, M. ; Kalden, J. R. ; Antoni, C. ; Macfarlane, J. D. ; Bijl, H. ; Woody, J. N. Lancet 1994, 344, 1105.
7. Evans, O. R. ; Xiong , R. G. ; Wang, Z. Y. ; Lin, W. B. Angew. Chem., Int. Ed. 1999, 38, 536.
8. (a) Service, R .F. Science 1994, 265, 1363.
9. (b) Amato, I. Science 1993, 259, 891.
10. Subramanian, S. ; Zaworotko, M. J. Angew. Chem. Int. Ed. Engl. 1995, 34, 2127.
11. (a) Venkaraman, D. ; Gardner, G. B. ; Lee, S. ; Moore, J. S. J. Am. Chem. Soc. 1995, 117, 11600.
12. (b) Moore, J. S. Nature 1995, 374, 495.
13. Ward, M. D. Nature 1995, 374, 764.
14. (a) Ward, M. D. Chem. Soc. Rev. 1995, 121.
15. (b) Sauvage, J. P. ; Collin, J. P. ; Chambron, J. C. ; Guillerez, S. ; Condret, C. ; Balzani, V. ; Barigelletti, F. ; DeCola , L. ; Flamigni, L. Chem. Rev. 1994, 94, 993.
16. Gopel, W. Nanostructures Based on Molecular Materials , Eds: Ziegler, Veinheim, VCH, 1992, p. 192.
17. Herrmann, W. A. ; Bohm, V. P. W. ; Reisinger, C. P. J. Orgnomet. Chem. 1999, 576, 23.
18. Angelo, J. A. ; Alexander, M. W. ; Cargill, T. ; John, P. M. ; Jon, A. M. ; Micheal, D. W. Inorg. Chem. 1995, 34, 4828.
19. Hoskins, B. F. ; Robson, R . ; Sutherland, E. E. J. Organomet. Chem. 1996, 575, 259.
20. Lin, J. T. ; Wu, J. J. ; Li, C. S. ; Wen, Y. S. ; Lin, K. J. Organometallics 1995, 15, 5028.
21. Bakvoine, F. ; Quan, L. G. ; Yanamoto, Y. Tetrahedron Lett. 1999, 40, 8351.
22. Wu, M. J. ; Chang, L. J. ; Wei, L. M. ; Lin, C. F. Tetrahedron 1999, 55, 13193.
23. LeCours, S. M. ; Guan, H. W. ; Dimagno, S. G. ; Wang, C. H. and Therien, M. J. J. Am. Chem. Soc. 1996, 118, 1497.
24. Nishihara, Y. ; Ikegashira, K. ; Hirabayashi, K. ; Ando, J. ; Mori, A. ; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
25. (a) Yeung, M, ; Ng, A. C. H. ; Drew, M. G. B. ; Vorpagel, E. ; Breitang, E. M. ; McMahon, R. J. ; Ng, D. K. P. J. Org. Chem. 1998, 63, 7143.
26. (b) LeCours, S. M. ; Philips, C. M. ; DePaula, J. C. ; Therien, M. J. J. Am. Chem. Soc. 1997, 119, 12578.
27. Changing solvents did not lead to any improvements. However, changing the leaving group from Br to I greatly facilitated the reaction and the product was obtained in high yields.
28. When the aryl carrying an ester group, the coupling reaction was effectively catalyzed by thiethylamine. Diethylamine, however, could catalyze the reaction only when the aryl carries hetero atoms, halogens, or cyano groups.