Pure Appl. Chem., 2012, Vol. 84, No. 4, pp. 1027-1037
http://dx.doi.org/10.1351/PAC-CON-11-08-21
Published online 2011-12-14
Copper-catalyzed alkyne-azide cycloaddition for the functionalization of fullerene building blocks
References
- 1a. F. Langa, J.-F. Nierengarten (Eds.). Fullerenes: Principles and Applications, 2nd ed., RSC Nanoscience and Nanotechnology Series, Cambridge (2011).
- 1b. D. M. Guldi, N. Martin (Eds.). Carbon Nanotubes and Related Structures: Synthesis, Characterization, Functionalization and Applications, Wiley-VCH, Weinheim (2010).
- 2. For selected reviews, see.
- 2a. D. M. Chem. Soc. Rev. 31, 22 (2002). ( . http://dx.doi.org/10.1039/b106962b)
- 2b. H. J. Phys. Chem. B 108, 6130 (2004). ( . http://dx.doi.org/10.1021/jp038036b)
- 2c. J.-F. Sol. Energy Mater. Sol. Cells 83, 187 (2004). .
- 2d. J.-F. New J. Chem. 28, 1177 (2004). ( . http://dx.doi.org/10.1039/b402661f)
- 2e. J. L. Chem. Soc. Rev. 34, 31 (2005). ( , N. Martin, D. M. Guldi. http://dx.doi.org/10.1039/b402417f)
- 2f. T. M. Chem. Commun. 109 (2007). ( , A. Gégout, J.-F. Nierengarten. http://dx.doi.org/10.1039/b609383c)
- 3. For selected reviews, see.
- 3a. T. Chem. Commun. 663 (1999). ( , M. Prato. http://dx.doi.org/10.1039/a809495k)
- 3b. E. Acc. Chem. Res. 36, 807 (2003). ( , H. Isobe. http://dx.doi.org/10.1021/ar030027y)
- 3c. S. Eur. J. Med. Chem. 38, 913 (2003). ( , T. Da Ros, G. Spalluto, M. Prato. http://dx.doi.org/10.1016/j.ejmech.2003.09.005)
- 4. A. Hirsch, M. Brettreich. Fullerenes: Chemistry and Reactions, Wiley-VCH, Weinheim (2005).
- 5. For selected examples, see.
- 5a. J.-F. Tetrahedron Lett. 40, 273 (1999). ( , D. Felder, J.-F. Nicoud. http://dx.doi.org/10.1016/S0040-4039(98)02379-X)
- 5b. D. New J. Chem. 24, 687 (2000). ( , H. Nierengarten, J.-P. Gisselbrecht, C. Boudon, E. Leize, J.-F. Nicoud, M. Gross, A. Van Dorsselaer, J.-F. Nierengarten. http://dx.doi.org/10.1039/b003345f)
- 5c. N. Chem.—Eur. J. 8, 2314 (2002). ( , G. Accorsi, D. Felder, J.-F. Nierengarten. http://dx.doi.org/10.1002/1521-3765(20020517)8:10<2314::AID-CHEM2314>3.0.CO;2-Z)
- 5d. U. New J. Chem. 33, 337 (2009). ( , J.-F. Nierengarten, F. Vögtle, A. Listorti, F. Monti, N. Armaroli. http://dx.doi.org/10.1039/b816336g)
- 6. For selected examples, see.
- 6a. U. Chem. Commun. 516 (2007). ( , A. Gégout, C. Duhayon, Y. Coppel, A. Saquet, J.-F. Nierengarten. http://dx.doi.org/10.1039/b614009b)
- 6b. B. J. Mater. Chem. 18, 1547 (2008). ( , A. Kaeser, U. Hahn, A. Gégout, P.-E. Brandli, C. Duhayon, Y. Coppel, A. Saquet, J.-F. Nierengarten. http://dx.doi.org/10.1039/b716506d)
- 7. For selected examples, see.
- 7a. J.-F. Angew. Chem., Int. Ed. 37, 1934 (1998). ( , C. Schall, J.-F. Nicoud. http://dx.doi.org/10.1002/(SICI)1521-3773(19980803)37:13/14<1934::AID-ANIE1934>3.0.CO;2-M)
- 7b. J.-F. Chem. Commun. 1545 (1998). ( , L. Oswald, J.-F. Nicoud. http://dx.doi.org/10.1039/a803434f)
- 7c. M. Tetrahedron Lett. 48, 8111 (2007). ( , J.-F. Nierengarten. http://dx.doi.org/10.1016/j.tetlet.2007.09.107)
- 7d. M. Eur. J. Org. Chem. 3715 (2009). ( , J. Iehl, I. Osinska, R. Louis, M. Holler, J.-F. Nierengarten. http://dx.doi.org/10.1002/ejoc.200900358)
- 8a. C. Angew. Chem., Int. Ed. 48, 4900 (2009). ( , R. Hoogenboom, U. S. Schubert. http://dx.doi.org/10.1002/anie.200900755)
- 8b. C. E. Angew. Chem., Int. Ed. 49, 1540 (2010). ( , C. N. Bowman, http://dx.doi.org/10.1002/anie.200903924)
- 8c. G. Chem. Soc. Rev. 39, 1536 (2010). ( , A. K. Kakkar. http://dx.doi.org/10.1039/b913281n)
- 8d. C. E. Chem. Soc. Rev. 39, 1355 (2010). ( , A. B. Lowe, C. N. Bowman. http://dx.doi.org/10.1039/b901979k)
- 9a. R. Pure Appl. Chem. 61, 613 (1989). ( . http://dx.doi.org/10.1351/pac198961040613)
- 9b. G. Chem. Ber. 100, 2494 (1967). ( , W. Szeimies, L. Moebius. http://dx.doi.org/10.1002/cber.19671000806)
- 9c. C. W. Tornøe, M. Meldal. Proceedings of the 2nd International and 17th American Peptide Symposium, Peptides: The Waves of the Future, M. Lebl, R. A. Houghten (Eds.), San Diego, 263 (2001).
- 9d. V. V. Angew. Chem., Int. Ed. 41, 2596 (2002). ( , L. G. Green, V. V. Fokin, K. B. Sharpless. http://dx.doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4)
- 10. H. C. Angew. Chem., Int. Ed. 40, 2004 (2001). ( , M. G. Finn, K. B. Sharpless. http://dx.doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5)
- 11. M. J. Am. Chem. Soc. 115, 1148 (1993). ( , Q. C. Li, F. Wudl, V. Lucchini. http://dx.doi.org/10.1021/ja00056a049)
- 12. J. Tetrahedron Lett. 49, 4063 (2008). ( , R. Pereira de Freitas, J.-F. Nierengarten. http://dx.doi.org/10.1016/j.tetlet.2008.04.064)
- 13. R. Tetrahedron 64, 11409 (2008). ( , J. Iehl, B. Delavaux-Nicot, J.-F. Nierengarten. http://dx.doi.org/10.1016/j.tet.2008.09.047)
- 14. For other examples of CuAAC reactions from fullerene building blocks, see.
- 14a. H. Org. Lett. 9, 4611 (2007). ( , K. Cho, N. Solin, D. B. Werz, P. H. Seeberger, E. Nakamura. http://dx.doi.org/10.1021/ol702128z)
- 14b. W.-B. Macromolecules 41, 515 (2008). ( , Y. Tu, R. Ranjan, R. M. Van Horn, S. Leng, J. Wang, M. J. Polce, C. Wesdemiotis, R. P. Quirk, G. R. Newkome, S. Z. D. Cheng. http://dx.doi.org/10.1021/ma702345r)
- 14c. I. M. Tetrahedron 64, 11420 (2008). ( , N. Zhou, L. Wang, Y. Zhao. http://dx.doi.org/10.1016/j.tet.2008.08.083)
- 15. F. Helv. Chim. Acta 80, 343 (1997). ( , P. Seiler, L. Isaacs, J.-F. Nierengarten, R. F. Haldimann, F. Diederich, T. Mordasini-Denti, W. Thiel, C. Boudon, J.-P. Gisselbrecht, M. Gross. http://dx.doi.org/10.1002/hlca.19970800203)
- 16a. J.-F. Tetrahedron Lett. 39, 5747 (1998). ( , C. Schall, J.-F. Nicoud, B. Heinrich, D. Guillon. http://dx.doi.org/10.1016/S0040-4039(98)01134-4)
- 16b. D. Angew. Chem., Int. Ed. 39, 201 (2000). ( , J.-L. Gallani, D. Guillon, B. Heinrich, J.-F. Nicoud, J.-F. Nierengarten. http://dx.doi.org/10.1002/(SICI)1521-3773(20000103)39:1<201::AID-ANIE201>3.0.CO;2-A)
- 16c. J.-F. J. Am. Chem. Soc. 123, 9743 (2001). ( , J.-F. Eckert, Y. Rio, M. P. Carreon, J.-L. Gallani, D. Guillon. http://dx.doi.org/10.1021/ja010155m)
- 16d. S. J. Org. Chem. 68, 9787 (2003). ( , Y. Rio, F. Cardinali, C. Bourgogne, J.-L. Gallani, J.-F. Nierengarten. http://dx.doi.org/10.1021/jo035040a)
- 17. J. Tetrahedron Lett. 50, 2245 (2009). ( , I. Osinska, R. Louis, M. Holler, J.-F. Nierengarten. http://dx.doi.org/10.1016/j.tetlet.2009.02.185)
- 18. J. J. Mater. Chem. 21, 1562 (2011). ( , M. Vartanian, M. Holler, J.-F. Nierengarten, B. Delavaux-Nicot, J.-M. Strub, A. Van Dorsselaer, Y. Wu, J. Mohanraj, K. Yoosaf, N. Armaroli. http://dx.doi.org/10.1039/c0jm02310h)
- 19a. D. Acc. Chem. Res. 34, 40 (2001). ( , T. A. Moore, A. L. Moore. http://dx.doi.org/10.1021/ar9801301)
- 19b. D. M. Chem. Soc. Rev. 31, 22 (2002). ( . http://dx.doi.org/10.1039/b106962b)
- 19c. D. I. C. R. Chimie 9, 892 (2006). ( , K. Li, D. M. Guldi. http://dx.doi.org/10.1016/j.crci.2005.11.013)
- 19d. A. C. R. Chimie 9, 944 (2006). ( , C. Sooambar, M. Prato. http://dx.doi.org/10.1016/j.crci.2005.11.018)
- 19e. J.-F. J. Porphyrins Phthalocyanines 12, 1022 (2008). ( . http://dx.doi.org/10.1142/S108842460800039X)
- 19f. R. J. Mater. Chem. 18, 1440 (2008). ( , F. D’Souza. http://dx.doi.org/10.1039/b717502g)
- 20. For a review on fullerene hexa-adducts, see: A. Eur. J. Org. Chem. 829 (2001). ( , O. Vostrowski. http://dx.doi.org/10.1002/1099-0690(200103)2001:5<829::AID-EJOC829>3.0.CO;2-V)
- 21. A. J. Am. Chem. Soc. 116, 9385 (1994). ( , I. Lamparth, T. Grösser, H. R. Karfunkel. http://dx.doi.org/10.1021/ja00099a088)
- 22a. H. Org. Lett. 7, 859 (2005). ( , A. Kitaygorodskiy, R. A. Carino, Y.-P. Sun. http://dx.doi.org/10.1021/ol0473851)
- 22b. H. Org. Lett. 8, 5641 (2006). ( , S. A. Haque, A. Kitaygorodskiy, M. J. Meziani, M. Torres-Castillo, Y.-P. Sun. http://dx.doi.org/10.1021/ol062391d)
- 23. J. Chem. Commun. 2450 (2008). ( , R. Pereira de Freitas, B. Delavaux-Nicot, J.-F. Nierengarten. http://dx.doi.org/10.1039/b804393k)
- 24. For other examples of post-functionalization of fullerene hexa-adducts, see.
- 24a. P. Chem. Commun. 1748 (2009). ( , S. Vanderheiden, T. Muller, S. Bräse. http://dx.doi.org/10.1039/b900367c)
- 24b. P. Chem.—Eur. J. 15, 11458 (2090). ( , C. Réthoré, T. Muller, S. Bräse. http://dx.doi.org/10.1002/chem.200902141)
- 24c. J. Chem. Commun. 46, 4160 (2010). ( , J.-F. Nierengarten. http://dx.doi.org/10.1039/c0cc00252f)
- 24d. P. Angew. Chem., Int. Ed. 50, 2364 (2011). , E. Maisonhaute, C. Amatore, B. Delavaux-Nicot, J. Iehl, J.-F. Nierengarten.
- 25. J. Chem.—Eur. J. 15, 7306 (2009). ( , J.-F. Nierengarten. http://dx.doi.org/10.1002/chem.200901291)
- 26. X. Chem.—Eur. J. 3, 561 (1997). ( , H. Schönberger, A. Hirsch. http://dx.doi.org/10.1002/chem.19970030411)
- 27. D. Chem. Commun. 47, 4640 (2011). ( , M. Holler, J. Iehl, J.-F. Nierengarten, M. Nothisen, E. Morin, J.-S. Remy. http://dx.doi.org/10.1039/c0cc05783e)
- 28. M. New J. Chem. 31, 1111 (2007) and refs. therein. ( , S. Eisler, F. Diederich. http://dx.doi.org/10.1039/b614877h)
- 29. J.-F. Chem. Commun. 46, 3860 (2010). ( , J. Iehl, V. Oerthel, M. Holler, B. M. Illescas, A. Muñoz, N. Martín, J. Rojo, M. Sánchez-Navarro, S. Cecioni, S. Vidal, K. Buffet, M. Durka, S. P. Vincent. http://dx.doi.org/10.1039/c0cc00034e)
- 30. M. Chem. Commun. 47, 1321 (2011). ( , K. Buffet, J. Iehl, M. Holler, J.-F. Nierengarten, J. Taganna, J. Bouckaert, S. P. Vincent. http://dx.doi.org/10.1039/c0cc04468g)
- 31. S. Chem.—Eur. J. 17, 3252 (2011). ( , V. Oerthel, J. Iehl, M. Holler, D. Goyard, J.-P. Praly, A. Imberty, J.-F. Nierengarten, S. Vidal. http://dx.doi.org/10.1002/chem.201003258)
- 32. P. Angew. Chem., Int. Ed. 49, 5753 (2010). ( , C. Decroocq, J. Iehl, M. Holler, D. Hazelard, T. Mena Barragán, C. Ortiz Mellet, J.‑F. Nierengarten. http://dx.doi.org/10.1002/anie.201002802)
- 33. J. Aust. J. Chem. 64, 153 (2011). ( , M. Holler, J.-F. Nierengarten, K. Yoosaf, J. M. Malicka, N. Armaroli, J.-M. Strub, A. Van Dorsselaer, B. Delavaux-Nicot. http://dx.doi.org/10.1071/CH10319)
- 34. M. Chem.—Eur. J. 17, 766 (2011). ( , A. Munoz, B. M. Illescas, J. Rojo, N. Martin. http://dx.doi.org/10.1002/chem.201002816)
- 35. Y. M. Adv. Carbohydr. Chem. Biochem. 63, 165 (2010). ( , R. Roy. http://dx.doi.org/10.1016/S0065-2318(10)63006-5)