Regioselective synthesis of 1,4-di(organo)[60]fullerenes through DMF-assisted monoaddition of silylmethyl Grignard reagents and subsequent alkylation reaction

Journal of the American Chemical Society

Volumn 130, Issue 46, 2008, Pages 15429-15436

  Matsuo, Yutaka ^a   Iwashita, Akihiko ^b   Abe, Yoko ^a   Li, Chang Zhi ^a   Matsuo, Keiko ^b   Hashiguchi, Masahiko ^a   Nakamura, Eiichi ^a,b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHEMICAL COMPOUNDS; CHEMICAL PROPERTIES; DIMETHYLFORMAMIDE; FULLERENES; HYDROCARBONS; NANOSTRUCTURES; SILANES;

[60] FULLERENES; ALKYLATION REACTIONS; GOOD YIELDS; GRIGNARD REAGENTS; HIGH YIELDS; ISOLATED YIELDS; MONOADDITION; REGIOSELECTIVE SYNTHESES;

AROMATIC HYDROCARBONS;

1 (DIMETHYLPHENYLSILYLMETHYL) 1,9 DIHYDRO[5,6]FULLERENE; 1,7 BIS(DIMETHYLPHENYLSILYLMETHYL) 1,7 DIHYDRO[5,6]FULLRENE; FULLERENE DERIVATIVE; GRIGNARD REAGENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKYLATION; ARTICLE; CRYSTAL STRUCTURE; ELECTRON; ELECTRON TRANSPORT; PROTON TRANSPORT; SOLUBILITY; SYNTHESIS; TEMPERATURE; THERMOSTABILITY;

EID: 56449124782     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8041299     Document Type: Article

References (66)

1. (a) Hummelen, J. C.; Knight, B. W.; LePeq, F.; Wudl, F.; Yao, J.; Wilkins, C. L. J. Org. Chem. 1995, 60, 532.
2. (b) Li, G.; Shrotriya, V.; Huang, J.; Yao, Y.; Moriarty, T.; Emery, K.; Yang, Y. Nat. Mater. 2005, 4, 864.
3. (a) Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1993, 115, 9798.
4. (b) Prato, M.; Maggini, M. Acc. Chem. Res. 1998, 31, 519.
5. (c) Yang, C.; Li, Y.; Hou, J.; He, C.; Tan, Z.; Fan, B.; Zhou, Y.; Sun, Q.; Li, Y.; Li, Y.; Zhu, D. Polym. Adv. Technol. 2006, 17, 500.
6. (a) Waldauf, C.; Schilinsky, P.; Perisutti, M.; Hauch, J.; Brabec, C. J. Adv. Mater. 2003, 15, 2084.
7. (b) Anthopoulos, T. D.; Tanase, C.; Setayesh, S.; Meijer, E. J.; Hummelen, J. C.; Blom, P. W. M.; de Leeuw, D. M. Adv. Mater. 2004, 16, 2174.
8. (a) Sariciftci, N. S.; Braun, D.; Zhang, C.; Srdanov, V. I.; Heeger, A. J.; Stucky, G.; Wudl, F. Appl. Phys. Lett. 1993, 62, 585.
9. (b) Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789.
10. Reed, C. A.; Bolskar, R. D. Chem. Rev. 2000, 100, 1075.
11. (a) Guldi, D. M.; Neta, P.; Asmus, K.-D. J. Phys. Chem. 1994, 98, 4617.
12. (b) Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537.
13. (c) Guldi, D. M.; Fukuzumi, S. The Small Reorganization Energy of Fullerenes. In Fullerenes: From Synthesis to Optoelectronic Properties; Guldi, D. M., Martin, N., Ed.; Kluwer: Dordrecht, 2003; pp 237-265.
14. Singh, T. B.; Marjanovic, N.; Matt, G. J.; Günes, S.; Sariciftci, N. S.; Ramil, A. M.; Andreev, A.; Sitter, H.; Schwödiauer, R.; Bauer, S. Org. Electron. 2005, 6, 105.
15. (a) Sawamura, M.; Kawai, K.; Matsuo, Y.; Kanie, K.; Kato, T.; Nakamura, E. Nature 2002, 419, 702.
16. (b) Matsuo, Y.; Muramatsu, A.; Hamasaki, R.; Mizoshita, N.; Kato, T.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 432.
17. (c) Matsuo, Y.; Muramatsu, A.; Kamikawa, Y.; Kato, T.; Nakamura, E. J. Am. Chem. Soc. 2006, 128, 9586.
18. (d) Zhong, Y.-W.; Matsuo, Y.; Nakamura, E. J. Am. Chem. Soc. 2007, 129, 3052.
19. (a) Nagashima, H.; Terasaki, H.; Kimura, E.; Nakajima, K.; Itoh, K. J. Org. Chem. 1994, 59, 1246.
20. (b) Nagashima, H.; Terasaki, H.; Saito, Y.; Jinno, K.; Itoh, K. J. Org. Chem. 1995, 60, 4966.
21. (c) Nagashima, H.; Saito, M.; Kato, Y.; Goto, H.; Osawa, E.; Haga, M.; Itoh, K. Tetrahedron 1996, 52, 5053.
22. Matsuo, Y.; Nakamura, E. Inorg. Chim. Acta 2006, 359, 1979.
23. (a) Caron, C.; Subramanian, R.; D'Souza, F.; Kim, J.; Kutner, W.; Jones, M. T.; Kadish, K. M. J. Am. Chem. Soc. 1993, 113, 8505.
24. (b) Subramanian, R.; Boulas, P.; Vijayashree, M. N.; D'Souza, F.; Jones, M. T.; Kadish, K. M. J. Chem. Soc., Chem. Commun. 1994, 1847.
25. (c) Keshavarz, K. M.; Knight, B.; Srdanov, G.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 11371.
26. (d) Subramanian, R.; Kadish, K. M.; Vijayashree, M. N.; Gao, X.; Jones, M. T.; Miller, M. D.; Krause, K. L.; Suenobu, T.; Fukuzumi, S. J. Phys. Chem. 1996, 100, 16327.
27. (e) Fukuzumi, S.; Suenobu, T.; Hirasaka, T.; Arakawa, R.; Kadish, K. M. J. Am. Chem. Soc. 1998, 120, 9220.
28. Fagan, P. J.; Krusic, P. J.; Evans, D. H.; Lerke, S. A.; Johnston, E. J. Am. Chem. Soc. 1992, 114, 9697.
29. (a) Hirsch, A.; Soi, A.; Karfunkel, H. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 766.
30. (b) Hirsch, A.; Grosser, T.; Skiebe, A. Soi, A. Chem. Ber. 1993, 126, 1061.
31. (c) Hirsch, A. Synthesis 1995, 895.
32. (d) Hirsch, A.; Brettreich, M. Fullerenes: Chemistry and Reactions; Wiley-VCH: Weinheim, 2004.
33. Anderson, H. L.; Faust, R.; Rubin, Y.; Diederich, F. Angew Chem. Int. Ed. 1994, 33, 1366.
34. (a) Komatsu, K.; Murata, Y.; Takimoto, N.; Mori, S.; Sugita, N.; Wan, T. S. M. J. Org. Chem. 1994, 59, 6101.
35. (b) Murata, Y.; Komatsu, K.; Wan, T. S. M. Tetrahedron Lett. 1996, 37, 7061.
36. (c) Murata, Y.; Shiro, M.; Komatsu, K. J. Am. Chem. Soc. 1997, 119, 8117.
37. (d) Kitagawa, T.; Tanaka, T.; Takata, Y.; Takeuchi, K.; Komatsu, K. Tetrahedron 1997, 53, 9965.
38. (e) Kitagawa, T.; Lee, Y.; Hanamura, M.; Sakamoto, H.; Konno, H.; Takeuchi, K.; Komatsu, K. Chem. Commun. 2002, 3062.
39. (a) Iwashita, A.; Matsuo, Y.; Nakamura, E. Angew. Chem., Int. Ed. 2007, 46, 3513.
40. (b) Matsuo, Y.; Zhang, Y.; Nakamura, E. Org. Lett. 2008, 10, 1251.
41. Nambo, M.; Noyori, R.; Itami, K. J. Am. Chem. Soc. 2007, 129, 8080.
42. Matsuo, Y.; Tahara, K.; Morita, K.; Matsuo, K.; Nakamura, E. Angew. Chem., Int. Ed. 2007, 46, 2844.
43. 3) (HPLC area ratios). See Supporting Information for the details of this control experiment.
44. Nakamura, E.; Matsuo, Y.; Iwashita, A. PCT Int. Appl. WO 2008059771.
45. (a) Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1989, 179.
46. (b) Desiraju, G. R. Chem. Commun. 2005, 2995.
47. 2. See ref 16a.
48. Birkofer, L.; Stuhl, O. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; pp 655-761.
49. Silverman, G. S.; Rakita, P. E. Handbook of Grignard Reagents, Marcel Dekker, Inc.: New York, 1996.
50. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 3rd ed.; Wiley-VCH: Weinheim, 2003; pp 93-145.
51. Matsuo, Y.; Nakamura, E. J. Am. Chem. Soc. 2005, 127, 8457.
52. Meire, M. S.; Bergosh, R. G.; Gallagher, M. E.; Spielmann, H. P.; Wang, Z. J. Org. Chem. 2002, 67, 5946.
53. Toganoh, M.; Matsuo, Y.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13974.
54. Hamasaki, R.; Matsuo, Y.; Nakamura, E. Chem. Lett. 2004, 33, 328.
55. (a) Schick, G.; Kampe, K.-D.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 2023.
56. (b) Meier, M. S.; Bergosh, R. G.; Gallagher, M. E.; Spielmann, H. P.; Wang, Z. J. Org. Chem. 2002, 67, 5946.
57. (a) Sawamura, M.; Toganoh, M.; Suzuki, K.; Hirai, A.; Iikura, H.; Nakamura, E. Org. Lett. 2000, 2, 1919.
58. (b) Toganoh, M.; Suzuki, K.; Udagawa, R.; Hirai, A.; Sawamura, M.; Nakamura, E. Org. Biomol. Chem. 2003, 1, 2604.
59. Matsuo, Y.; Nakamura, E. Chem. Rev. 2008, 108, 3016.
60. Corriu, R.; Jutzi, P. Tailor-Made Silicon-Oxygen Compounds: From Molecules to Materials; Vieweg: Wiesbaden, 1995; pp 75-86.
61. Sawamura, M.; Toganoh, M.; Iikura, H.; Matsuo, Y.; Hirai, A.; Nakamura, E. J. Mater. Chem. 2002, 12, 2109.
62. Toganoh, M.; Matsuo, Y.; Nakamura, E. J. Organomet. Chem. 2003, 683, 295.
63. (a) Chikamatsu, M.; Nagamatsu, S.; Yoshida, Y.; Saito, K.; Yase, K.; Kikuchi, K. Appl. Phys. Lett. 2005, 87, 203504.
64. (b) Kusai, H.; Nagano, T.; Imai, K.; Kubozono, Y.; Sako, Y.; Takaguchi, Y.; Fujiwara, A.; Akima, N.; Iwasa, Y.; Hino, S. Appl. Phys. Lett. 2006, 88, 173509.
65. Wong, W.-Y.; Wang, X.-Z.; He, Z.; Djurii, A. B.; Yip, C.-T.; Cheung, K.-Y.; Wang, H.; Mak, C. S. K.; Chan, W.-K. Nat. Mater. 2007, 6, 521.
66. Blom, P. W. M.; de Jong, M. J. M.; Vleggaar, J. J. M. Appl. Phys. Lett. 1996, 68, 3308.