Palladium-catalyzed selective and sequential functionalization of 2,4,6-trihalopyridine rings: Synthesis of ethynylpyridine polymers directly joined with aza-crown ethers

Heterocycles

Volumn 84, Issue 1, 2011, Pages 355-360

  Takashima, Shunsuke ^a   Yamamoto, Tsuyoshi ^a   Abe, Hajime ^a   Inouye, Masahiko ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84862909344     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-11-S(P)62     Document Type: Article

References (33)

1. C. Pedersen,J. Am. Chem. Soc.,1967, 89,2495;
2. E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, and D. J. Cram, J. Am. Chem. Soc., 1973, 95, 2692.
3. S. Shinkai and O. Manabe, Top. Curr. Chem., 1984, 121, 67;
4. G. W. Gokel, W. M. Leevy, and M. E. Weber, Chem. Rev., 2004, 104, 2723;
5. V. Balzani, M. Venturi, and A. Credi, Molecular Devices and Machines, Wiley-VCH, Weinheim, 2003;
6. E. R. Kay, D. A. Leigh, and F. Zerbetto, Angew. Chem. Int. Ed., 2007, 46, 72;
7. P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, and D. J. Williams, Chem. Eur. J., 1996, 2, 709;
8. S. J. Rowan and J. F. Stoddart, Polym. Adv. Technol., 2002, 13, 777;
9. W. R. Dichtel, O. S. Miljanic, W. Zhang, J. M. Spruell, K. Patel, I. Aprahamian, J. R. Heath, and J. F. Stoddart, Acc. Res. Chem., 2008, 41, 1750;
10. F. Huang and H. W. Gibson, Prog. Polym. Sci., 2005, 30, 982.
11. T. Miyagawa, M. Yamamoto, R. Muraki, H. Onouchi, and E. Yashima, J. Am. Chem. Soc., 2007, 129, 3676;
12. R. Sakai, T. Satoh, R. Kakuchi, H. Kaga, and T. Kakuchi, Macromolecules, 2003, 36, 3709;
13. R. Kakuchi, R, Sakai, I. Otsuka, T. Satoh, H. Kaga, and T. Kakuchi, Macromolecules, 2005, 38, 9441.
14. M. Inouye, M. Waki, and H. Abe, J. Am. Chem. Soc., 2004, 126, 2022;
15. H. Abe, N. Masuda, M. Waki, and M. Inouye, J. Am. Chem. Soc., 2005, 127, 16189;
16. M. Waki, H. Abe, and M. Inouye, Chem. Eur. J., 2006, 12, 7839;
17. M. Waki, H. Abe, and M. Inouye, Angew. Chem. Int. Ed., 2007, 46, 3059;
18. H. Abe, S. Takashima, T. Yamamoto, and M. Inouye, Chem. Commun., 2009, 2121;
19. S. Takashima, H. Abe, and M. Inouye, Chem. Commun., 2011, 47, 7455.
20. M. G. Organ, M. Abdel-Hadi, S. Avola, I. Dubovyk, N. Hadei, E. A. B. Kantchev, C. J. O'Brien, M. Sayah, and C. Valente, Chem. Eur. J., 2008, 14, 2443.
21. M. Schlosser, C. Bobbio, and T. Rausis, J. Org. Chem., 2005, 70, 2494.
22. C. Meyers, B. U. W. Maes, K. T. J. Loones, G. Bal, G. L. F. Lemiére, and R. A. Dommisse, J. Org. Chem., 2004, 69, 6010.
23. -1;
24. 3) δ 6.52 (s, 2 H), 3.74-3.60 (m, 24 H);
25. 3) δ 156.0, 150.5, 104.9, 70.9, 70.7, 70.6, 68.1, 51.1, 27.5;
26. +): 409.1297; Found: 409.1301
27. D. Gelman and S. L. Buchwald, Angew. Chem. Int. Ed., 2003, 42, 5993.
28. -1;
29. 3) δ 6.68 (s, 2 H), 3.78-3.58 (m, 24 H), 0.98 (s, 18 H), 0.18 (s, 12 H);
30. 3) δ 152.6, 143.0, 110.0, 105.1, 91.0, 70.8, 70.63, 70.58, 68.2, 50.4, 26.2, 16.7, -4.6;
31. +): 617.3806; Found: 617.3834
32. H. Abe, H. Machiguchi, S. Matsumoto, and M. Inouye, J. Org. Chem., 2008, 73, 4650.
33. 3) δ 7.13 (br s, 4n H), 6.90 (br s, 2n H), 4.02 (br s, 4n H), 3.67 (br s, 24n H), 1.78 (br s, 4n H), 1.52-1.18 (m, 20n H), 0.90 (br s, 6n H)