Solvent-free synthesis of N-arylfulleropyrrolidine derivatives without using phase-transfer catalyst under microwave irradiation

Synthetic Communications

Volumn 40, Issue 4, 2010, Pages 580-586

  Jin, Bo ^a,b   Peng, Ru Fang ^a   Yang, Wen Ning ^a   Wang, Kai ^a   Yuan, Bang Qun ^a   Chu, Shi Jin ^a  

^a SOUTHWEST UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b BEIJING INSTITUTE OF TECHNOLOGY   (China)

Author keywords

Fullerene; Fulleropyrrolidine; Microwave irradiation; N Arylation; Solvent free

Indexed keywords

FULLERENE DERIVATIVE; PYRROLIDINE DERIVATIVE; SOLVENT;

ARTICLE; ARYLATION; CATALYST; MICROWAVE RADIATION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 76149106148     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903007061     Document Type: Article

References (26)

1. Taylor, R.; Walton, D. R. M. The chemistry of fullerenes. Nature 1993, 363, 685-693.
2. Hirsch, A. The Chemistry of the Fullerenes; Thieme: Stuttgart, 1994.
3. Diederich, F.; Thilgen, C. Covalent fullerene chemistry. Science 1996, 271, 317-324.
4. Thilgen, C; Diederich, F. The higher fullerenes: Covalent chemistry and chirality. Top. Curr. Chem. 1999, 199, 135-171.
5. Nakamura, E.; Isobe, H. Functionalized fullerenes in water: The first 10 years of their chemistry, biology, and nanoscience. Acc. Chem. Res. 2003, 36, 807-815.
6. Nierengarten, J. F.; Martin, N.; Fowler, P. Fullerene Chemistry; Elsevier SAS: Paris, 2006.
7. Nazario, M.; Margarita, A.; Salvatore, F.; Angel, M. D. New reactions in fullerene chemistry. Synlett 2007, 20, 3077-3095.
8. Prato, M. Fullerene materials. Top. Curr. Chem. 1999, 199, 173-187.
9. 0: Advancements and future prospects. Russ. Chem. Bull. Int. Ed. 2002, 51, 367-443.
10. Peng, R. F.; Wang, G. W.; Shen, Y. B.; Li, Y. J.; Zhang, T. H.; Liu, Y. C; Murata, Y.; Komatsu, K. Solvent-free reactions of fullerenes with diethyl bromomalonate in the presence of inorganic bases under high-speed vibration milling conditions. Synth. Commun. 2004, 34, 2117-2126.
11. 80: Pronounced chemical shift differences of the geminal protons on the pyrrolidine ring. J. Org. Chem. 2005, 70, 5092-5097.
12. Quintiliani, M.; Kahnt, A.; Wofle, T.; Hieringer, W.; Vazquez, P.; Goling, A.; Guldi, D. M.; Torres, T. Synthesis and photoinduced electron-transfer properties of phthalocya-nine-[60]fullerene conjugates. Chem. Eur. J. 2008, 14, 3765-3775.
13. Baffreau, J.; Ordronneau, L.; Leroy-Lhez, S.; Hudhomme, P. Synthesis of perylene-3,4-mono(dicarboximide)-fullerene C60 dyads as new light-harvesting systems. J. Org. Chem. 2008, 73, 6142-6147.
14. Prato, M.; Maggini, M. Fulleropyrrolidines: A family of full-fledged fullerene derivatives. Acc. Chem. Res. 1998, 31, 519-526.
15. 0 and amino acid esters. J. Org. Chem. 2004, 69, 5800-5802.
16. Wang, G. W.; Chen, X. P.; Cheng, X. Unexpected reactions of [60]fullerene involving tertiary amines and insight into the reaction mechanisms. Chem. Eur. J. 2006, 12, 7246-7253.
17. 60: Synthesis, characterization, and functionalization of fullerene pyrrolidines. J. Am. Chem. Soc. 1993, 115, 9798-9799.
18. Maggini, M.; Karlsson, A.; Pasimeri, L.; Scorrano, G.; Prato, M.; Valli, L. Synthesis of N-acylated fulleropyrrolidines: New materials for the preparation of Langmuir-Blodgett films containing fullerenes. Tetrahedron Lett. 1994, 35, 2985-2988.
19. de la Cruz, P.; de la Hoz, A.; Font, L. M.; Langa, F.; Pérez-Rodŕiguez, M. C. Solvent-free phase transfer catalysis under microwaves in fullerene chemistry. A convenient preparation of N-alkylpyrrolidino[60]fullerenes. Tetrahedron Lett. 1998, 39, 6053-6056.
20. Deviprasad, G. R.; Rahman, M. S.; D'Souza, F. N-(2,4-Dinitrophenyl)-2- phenylfullero-pyrrolidine: An electroactive organofullerene dyad. Chem. Commun. 1999, 849-850.
21. Erdélyi, M.; Gogoll, A. Rapid microwave promoted sonogashira coupling reactions on solid phase. J. Org. Chem. 2003, 68, 6431-6434.
22. Zhang, J. M.; Yang, W.; He, P.; Zhu, S. Z.; Wang, S. Microwave-promoted one-pot three-component reaction to [60]fulleropyrrolidine derivatives. Synth. Commun. 2005, 35, 89-96.
23. Seipel, K. R.; Platt, Z. H.; Nguyen, M.; Holland, A. W. Microwave-assisted synthesis of phenylene-bridged aminophosphine ligands: Acceleration of N-arylation and aryl fluoride phosphorylation reactions. J. Org. Chem. 2008, 73, 4291-4294.
24. 60-acceptor dyads. Eur. J. Org. Chem. 1999, 3433-3436.
25. Langa, F.; de la Cruz, P.; Esṕildora, E.; Garćia, J. J.; Pérez, M. C.; de la Hoz, A. Fullerene chemistry under microwave irradiation. Carbon 2000, 38, 1641-1646.
26. 60: A new form of carbon. Nature 1990, 347, 354-358.