Copper-catalyzed alkyne-azide cycloaddition for the functionalization of fullerene building blocks

Pure and Applied Chemistry

Volumn 84, Issue 4, 2012, Pages 1027-1037

  Nierengarten, Jean François ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Alkynes; Azides; Cycloadditions; Fullerene chemistry; Triazole

Indexed keywords

ALKYNES; AZIDES; CYCLOADDITIONS; FULLERENE CHEMISTRY; TRIAZOLE;

CATALYSIS; COPPER; CYCLOADDITION; FULLERENES; NITROGEN COMPOUNDS;

ACETYLENE;

EID: 84859126817     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/PAC-CON-11-08-21     Document Type: Article

References (70)

1. F. Langa, J.-F. Nierengarten (Eds.). Fullerenes: Principles and Applications, 2nd ed., RSC Nanoscience and Nanotechnology Series, Cambridge (2011)
2. D. M. Guldi, N. Martin (Eds.). Carbon Nanotubes and Related Structures: Synthesis, Characterization, Functionalization and Applications, Wiley-VCH, Weinheim (2010).
3. D. M. Guldi. Chem. Soc. Rev. 31, 22 (2002)
4. H. Imahori. J. Phys. Chem. B 108, 6130 (2004)
5. J.-F. Nierengarten. Sol. Energy Mater. Sol. Cells 83, 187 (2004)
6. J.-F. Nierengarten. New J. Chem. 28, 1177 (2004)
7. J. L. Segura, N. Martin, D. M. Guldi. Chem. Soc. Rev. 34, 31 (2005)
8. T. M. Figueira-Duarte, A. Gégout, J.-F. Nierengarten. Chem. Commun. 109 (2007).
9. T. Da Ros, M. Prato. Chem. Commun. 663 (1999)
10. E. Nakamura, H. Isobe. Acc. Chem. Res. 36, 807 (2003)
11. S. Bosi, T. Da Ros, G. Spalluto, M. Prato. Eur. J. Med. Chem. 38, 913 (2003).
12. A. Hirsch, M. Brettreich. Fullerenes: Chemistry and Reactions, Wiley-VCH, Weinheim (2005).
13. J.-F. Nierengarten, D. Felder, J.-F. Nicoud. Tetrahedron Lett. 40, 273 (1999)
14. D. Felder, H. Nierengarten, J.-P. Gisselbrecht, C. Boudon, E. Leize, J.-F. Nicoud, M. Gross, A. Van Dorsselaer, J.-F. Nierengarten. New J. Chem. 24, 687 (2000)
15. N. Armaroli, G. Accorsi, D. Felder, J.-F. Nierengarten. Chem.-Eur. J. 8, 2314 (2002)
16. U. Hahn, J.-F. Nierengarten, F. Vögtle, A. Listorti, F. Monti, N. Armaroli. New J. Chem. 33, 337 (2009).
17. U. Hahn, A. Gégout, C. Duhayon, Y. Coppel, A. Saquet, J.-F. Nierengarten. Chem. Commun. 516 (2007)
18. B. Delavaux-Nicot, A. Kaeser, U. Hahn, A. Gégout, P.-E. Brandli, C. Duhayon, Y. Coppel, A. Saquet, J.-F. Nierengarten. J. Mater. Chem. 18, 1547 (2008).
19. J.-F. Nierengarten, C. Schall, J.-F. Nicoud. Angew. Chem., Int. Ed. 37, 1934 (1998)
20. J.-F. Nierengarten, L. Oswald, J.-F. Nicoud. Chem. Commun. 1545 (1998)
21. M. Urbani, J.-F. Nierengarten. Tetrahedron Lett. 48, 8111 (2007)
22. M. Urbani, J. Iehl, I. Osinska, R. Louis, M. Holler, J.-F. Nierengarten. Eur. J. Org. Chem. 3715 (2009).
23. C. Remzi Becer, R. Hoogenboom, U. S. Schubert. Angew. Chem., Int. Ed. 48, 4900 (2009)
24. C. E. Hoyle, C. N. Bowman, Angew. Chem., Int. Ed. 49, 1540 (2010)
25. G. Franc, A. K. Kakkar. Chem. Soc. Rev. 39, 1536 (2010)
26. C. E. Hoyle, A. B. Lowe, C. N. Bowman. Chem. Soc. Rev. 39, 1355 (2010).
27. R. Huisgen. Pure Appl. Chem. 61, 613 (1989)
28. G. Huisgen, W. Szeimies, L. Moebius. Chem. Ber. 100, 2494 (1967)
29. 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)
30. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless. Angew. Chem., Int. Ed. 41, 2596 (2002).
31. H. C. Kolb, M. G. Finn, K. B. Sharpless. Angew. Chem., Int. Ed. 40, 2004 (2001).
32. M. Prato, Q. C. Li, F. Wudl, V. Lucchini. J. Am. Chem. Soc. 115, 1148 (1993).
33. J. Iehl, R. Pereira de Freitas, J.-F. Nierengarten. Tetrahedron Lett. 49, 4063 (2008).
34. R. Pereira de Freitas, J. Iehl, B. Delavaux-Nicot, J.-F. Nierengarten. Tetrahedron 64, 11409 (2008).
35. H. Isobe, K. Cho, N. Solin, D. B. Werz, P. H. Seeberger, E. Nakamura. Org. Lett. 9, 4611 (2007)
36. W.-B. Zhang, 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. Macromolecules 41, 515 (2008)
37. I. M. Mahmud, N. Zhou, L. Wang, Y. Zhao. Tetrahedron 64, 11420 (2008).
38. F. Cardullo, P. Seiler, L. Isaacs, J.-F. Nierengarten, R. F. Haldimann, F. Diederich, T. Mordasini-Denti, W. Thiel, C. Boudon, J.-P. Gisselbrecht, M. Gross. Helv. Chim. Acta 80, 343 (1997).
39. J.-F. Nierengarten, C. Schall, J.-F. Nicoud, B. Heinrich, D. Guillon. Tetrahedron Lett. 39, 5747 (1998)
40. D. Felder, J.-L. Gallani, D. Guillon, B. Heinrich, J.-F. Nicoud, J.-F. Nierengarten. Angew. Chem., Int. Ed. 39, 201 (2000)
41. J.-F. Nierengarten, J.-F. Eckert, Y. Rio, M. P. Carreon, J.-L. Gallani, D. Guillon. J. Am. Chem. Soc. 123, 9743 (2001)
42. S. Zhang, Y. Rio, F. Cardinali, C. Bourgogne, J.-L. Gallani, J.-F. Nierengarten. J. Org. Chem. 68, 9787 (2003).
43. J. Iehl, I. Osinska, R. Louis, M. Holler, J.-F. Nierengarten. Tetrahedron Lett. 50, 2245 (2009).
44. J. Iehl, M. Vartanian, M. Holler, J.-F. Nierengarten, B. Delavaux-Nicot, J.-M. Strub, A. Van Dorsselaer, Y. Wu, J. Mohanraj, K. Yoosaf, N. Armaroli. J. Mater. Chem. 21, 1562 (2011).
45. D. Gust, T. A. Moore, A. L. Moore. Acc. Chem. Res. 34, 40 (2001)
46. D. M. Guldi. Chem. Soc. Rev. 31, 22 (2002)
47. D. I. Schuster, K. Li, D. M. Guldi. C. R. Chimie 9, 892 (2006)
48. A. Mateo-Alonso, C. Sooambar, M. Prato. C. R. Chimie 9, 944 (2006)
49. J.-F. Nierengarten. J. Porphyrins Phthalocyanines 12, 1022 (2008)
50. R. Chitta, F. D'Souza. J. Mater. Chem. 18, 1440 (2008).
51. A. Hirsch, O. Vostrowski. Eur. J. Org. Chem. 829 (2001).
52. A. Hirsch, I. Lamparth, T. Grösser, H. R. Karfunkel. J. Am. Chem. Soc. 116, 9385 (1994).
53. H. Li, A. Kitaygorodskiy, R. A. Carino, Y.-P. Sun. Org. Lett. 7, 859 (2005)
54. H. Li, S. A. Haque, A. Kitaygorodskiy, M. J. Meziani, M. Torres-Castillo, Y.-P. Sun. Org. Lett. 8, 5641 (2006).
55. J. Iehl, R. Pereira de Freitas, B. Delavaux-Nicot, J.-F. Nierengarten. Chem. Commun. 2450 (2008).
56. P. Pierrat, S. Vanderheiden, T. Muller, S. Bräse. Chem. Commun. 1748 (2009)
57. P. Pierrat, C. Réthoré, T. Muller, S. Bräse. Chem.-Eur. J. 15, 11458 (2090)
58. J. Iehl, J.-F. Nierengarten. Chem. Commun. 46, 4160 (2010)
59. P. Fortgang, E. Maisonhaute, C. Amatore, B. Delavaux-Nicot, J. Iehl, J.-F. Nierengarten. Angew. Chem., Int. Ed. 50, 2364 (2011).
60. J. Iehl, J.-F. Nierengarten. Chem.-Eur. J. 15, 7306 (2009).
61. X. Camps, H. Schönberger, A. Hirsch. Chem.-Eur. J. 3, 561 (1997).
62. D. Sigwalt, M. Holler, J. Iehl, J.-F. Nierengarten, M. Nothisen, E. Morin, J.-S. Remy. Chem. Commun. 47, 4640 (2011).
63. M. Guillot-Nieckowski, S. Eisler, F. Diederich. New J. Chem. 31, 1111 (2007) and refs. therein.
64. J.-F. Nierengarten, 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. Chem. Commun. 46, 3860 (2010).
65. M. Durka, K. Buffet, J. Iehl, M. Holler, J.-F. Nierengarten, J. Taganna, J. Bouckaert, S. P. Vincent. Chem. Commun. 47, 1321 (2011).
66. S. Cecioni, V. Oerthel, J. Iehl, M. Holler, D. Goyard, J.-P. Praly, A. Imberty, J.-F. Nierengarten, S. Vidal. Chem.-Eur. J. 17, 3252 (2011).
67. P. Compain, C. Decroocq, J. Iehl, M. Holler, D. Hazelard, T. Mena Barragán, C. Ortiz Mellet, J.-F. Nierengarten. Angew. Chem., Int. Ed. 49, 5753 (2010).
68. J. Iehl, M. Holler, J.-F. Nierengarten, K. Yoosaf, J. M. Malicka, N. Armaroli, J.-M. Strub, A. Van Dorsselaer, B. Delavaux-Nicot. Aust. J. Chem. 64, 153 (2011).
69. M. Sanchez-Navarro, A. Munoz, B. M. Illescas, J. Rojo, N. Martin. Chem.-Eur. J. 17, 766 (2011).
70. Y. M. Chabbre, R. Roy. Adv. Carbohydr. Chem. Biochem. 63, 165 (2010).