Facile synthesis of aryl ether dendrimer from unprotected AB2 building blocks using thionyl chloride as an activating agent

Organic Letters

Volumn 8, Issue 11, 2006, Pages 2321-2324

  Yamazaki, Natsuko ^a   Washio, Isao ^a   Shibasaki, Yuji ^a   Ueda, Mitsuru ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33745711812     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0605880     Document Type: Article

References (34)

1. Jiang, D.-L.; Aida. T. Nature 1997, 388, 1681.
2. Knapen, J. W. J.; Van der Made, A. W.; de Wilde, J. C.; Van Leeuwen, A. W.; Wijkens, P.; Grove, D. M.; Van Koten, G. Nature (London) 1994, 372, 659.
3. (a) Percec, V.; Cho, C. G.; Pugh, C.; Tomazos, D. Macromolecules 1992, 25, 1164.
4. (b) Percec, V.; Kawasumi, M. Macromolecules 1992, 25, 3843.
5. (c) Percec, V.; Johansson, G.; Heck, J.; Ungar, G.; Batty, S. J. Chem. Soc., Perkin Trans. 1 1993, 1411.
6. (d) Percec, V.; Chu, P.; Kawasumi, M. Macromolecules 1994, 27, 4441.
7. (e) Ponomarenko, S. A.; Eebrov, E. A.; Bobrovsky, A. Yu; Boiko, N. I.; Muzafarov, A. M.; Shibaev, V. P. Liq. Cryst. 1996, 21, 1.
8. (f) Busson, P.; Ihre, H.; Hult, A. J. Am. Chem. Soc. 1998, 120, 9070.
9. (a) Jansen, J. F. G. A.; de Brabander-Van den Berg, E. M. M.; Meijer, E. W. Science 1994, 266, 1226.
10. (b) Hawker, C. J.; Fréchet, J. M. J. J. Chem. Soc., Perkin Trans. 1 1992, 2459.
11. (a) Haensler, J.; Szoka, F. C. Bioconjugate Chem. 1993, 4, 372.
12. (b) Redemann, C. T.; Szoka, F. C. Bioconjugate Chem. 1996, 7, 703.
13. (c) Meijer, E. W.; Paulus, W.; Duncan, R. J. Controlled Release 2000, 65, 133.
14. (a) Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polym. J. 1985, 17, 117.
15. (b) Tomalia, D. A.; Naylor, A. N.; Goddard, W. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 138.
16. Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638.
17. Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1991, 113, 4252.
18. Kawaguchi, T.; Walker, K. L.; Wilkins, C. L.; More, J. S. J. Am. Chem. Soc. 1995, 117, 2159.
19. Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 82.
20. Spindler, R.; Fréchet, J. M. J., J. Chem. Soc., Perkin Trans. 1 1993, 913.
21. For reviews, see, for example: (a) Newcome, G. R.; Moorefield, C. N.; Vögtle, F. In Dendrimers and Dendrons, Concepts, Syntheses, Applications; VCH: Weinheim, Germany, 2001.
22. (b) Fréchet, J. M. J.; Tomalia, D. A. In Dendrimer and Other Dendritic Polymers; VCH: Weinheim, Germany, 2002.
23. Grayson, M. S., Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819.
24. Rannard, S. P.; Davis, N. J. J. Am. Chem. Soc. 2000, 122, 11729.
25. Okazaki, M.; Washio, I.; Shibasaki, Y.; Ueda, M. J. Am. Chem. Soc. 2003, 125, 8120.
26. Ueda, M.; Kameyama, A.; Hashimoto, K. Macromolecules 1988, 21, 19.
27. Washio, I.; Shibasaki, Y.; Ueda, M. Org. Lett. 2003, 5, 4159.
28. Forier, B.; Dehaen, W. Tetrahedron 1999, 55, 9829.
29. Basso, A.; Evans, B.; Pegg, N.; Bradley, M. Chem. Commun. 2001, 697.
30. Whitmore, F. C.; Karnatz, F. A.; Popkin, A. H. J. Am. Chem. Soc. 1938, 60, 2540.
31. (a) Balagurusamy, V. S. K.; Ungar, G.; Percec, V.; Johansson, G. J. Am. Chem. Soc. 1997, 119, 1539.
32. (b) Percec, V.; Cho, W.-D.; Mosier, P. E.; Ungar, G.; Yeardley, D. J. P. J. Am. Chem. Soc. 1998, 120, 11061.
33. (c) Percec, V.; Cho, W.-D.; Ungar, G.; Yeardley, D. J. P. J. Am. Chem. Soc. 2001, 123, 1302.
34. (d) Percec, V.; Mitchell, C. M.; Cho, W.-D.; Uchida, S.; Glodde, M.; Ungar, G.; Zeng, X.; Liu, Y.; Balagurusamy, V. S. K.; Heiney, P. A. J. Am. Chem. Soc. 2004, 126, 6078.