Persulfonylation of amines applied to the synthesis of higher generation dendrimers

Journal of Organic Chemistry

Volumn 73, Issue 9, 2008, Pages 3562-3565

  Lukin, Oleg ^a   Schubert, Dirk ^a   Müller, Claudia ^a   Corda, Mirza ^a   Kandre, Ramchandra ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMERS; FUNCTIONAL GROUPS; OLIGOMERS; OPTIMIZATION; SYNTHESIS (CHEMICAL);

AROMATIC OLIGOAMINES; PERIPHERAL GROUPS; PERSULFONYLATION;

AMINES;

AMINE; DENDRIMER; SULFONAMIDE;

ARTICLE; SYNTHESIS;

AMINES; DENDRIMERS; MOLECULAR STRUCTURE; SULFUR COMPOUNDS;

EID: 43449099161     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800179m     Document Type: Article

References (34)

1. Vögtle, F.; Richardt, G.; Werner, N. Dendritische Moleküle. Konzepte, Synthesen. Eigenschaften, Anwendungen; Teubner: Wiesbaden, Germany, 2007.
2. (a) Archut, A.; Vögtle, F. Chem. Soc. Rev. 1998, 27, 233-240.
3. (b) Smith, D. K.; Diederich, F. Chem. Eur. J. 1998, 4, 1351-1361.
4. (c) Bosman, A. W.; Jansen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665-1688.
5. (d) Fischer, M.; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38, 884-905.
6. (e) Newkome, G. R.; Moorefield, C. N.; Vögtle F. Dendrimers and Dendrons, Concepts, Syntheses, Applications; Wiley-VCH: Weinheim, Germany, 2001.
7. (f) Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819-3868.
8. Gao, C.; Yan, D. Prog. Polym. Sci. 2004, 29, 183-275.
9. (a) Schlüter, A. D.; Rabe, J. P. Angew. Chem., Int. Ed. 2000, 39, 864-883.
10. (b) Frauenrath, H. Prog. Polym. Sci. 2005, 30, 325-384.
11. (a) Hadjichristidis, N.; Pitsikalis, M.; Pispas, S.; Iatrou, H. Chem. Rev. 2001, 101, 3747-3792.
12. (b) Zhang, M.; Müller, A. H. E. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 3461-3481.
13. (c) Hadjichristidis, N; Iatrou, H.; Pitsikalis, M.; Mays, J. Prog. Polym. Sci. 2006, 31, 1068-1132.
14. (a) Nierengarten, J. F. Chem. Eur. J. 2000, 6, 3667-3670.
15. (b) Hecht, S.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2001, 40, 74-91.
16. (c) Haag, R. Chem. Eur. J. 2001, 7, 327-335.
17. (a) Dennig, J. Top. Curr. Chem. 2003, 228, 227-236.
18. (b) Lee, C. C.; MacKay, J. A.; Fréchet, J. M. J.; Szoka, F. C. Nat. Biotechnol. 2005, 23, 1517-1526.
19. (a) Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, C.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Macromolecules 1986, 19, 2466-2468.
20. (b) Brabander-van den Berg, E. M. M.; Meijer, E. W. Angew. Chem., Int. Ed. 1993, 32, 1308-1310.
21. (c) Wörner, C.; Mühlhaupt, R. Angew. Chem., Int. Ed. 1993, 32, 1306-1308.
22. (d) Newkome, G. R.; Yao, Z.; Baker, G. R.; Gupta, V. K J. Org. Chem. 1985, 50, 2003-2004.
23. (e) Launay, N.; Caminade, A.-M.; Lahana, R.; Majoral, J.-P. Angew. Chem., Int. Ed. 1994, 33, 1589-1592.
24. (f) Ruiz, J.; Latuente, H.; Marcen, S.; Ornelas, C.; Lazare, S.; Cloutet, E.; Blais, J.-C.; Astruc, D. J. Am. Chem. Soc. 2003, 125, 7250-7257.
25. (g) Jayamurugan, G.; Jayaraman, N. Tetrahedron 2006, 62, 9582-9588.
26. (h) Antoni, P.; Nyström, D.; Hawker, C. J.; Huit, A.; Malkoch, M. Chem. Commun. 2007, 2249, 2251.
27. For example, mass spectroscopic analysis of the 5th generation POPAM dendrimer revealed a structural purity of ca. 20%. See: Hummelen, J. C.; van Dongen, J. L. J.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1489-1493.
28. (a) Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638-7647.
29. (b) Xu, Z.; Moore, J. S. Angew. Chem., Int. Ed. 1993, 32, 246-248.
30. (c) Miller, T. M.; Neenan, T. X.; Zayas, R.; Bair, H. E. J. Am. Chem. Soc. 1992, 114, 1018-1025.
31. (a) Rannard, S. P.; Davis, N. J. J. Am. Chem. Soc. 2000, 122, 11739-11730.
32. (b) Okinawa, M.; Takeuchi, K.; Asai, M.; Ueda, M. Macromolecules 2002, 35, 6232-6238.
33. (c) Ornelas, C.; Aranzaes, J. R.; Cloutet, E.; Astruc, D. Org. Lett. 2006, 8, 2751-2753.
34. Lukin, O.; Gramlich, V.; Kandre, R.; Zhun, I.; Felder, T.; Schalley, C. A.; Dolgonos, G. J. Am. Chem. Soc. 2006, 128, 8964-8974.