Hypervalent iodine reagent mediated reaction of [60]fullerene with amines

Journal of Organic Chemistry

Volumn 78, Issue 23, 2013, Pages 12257-12262

  Miao, Chun Bao ^a   Lu, Xin Wei ^a   Wu, Ping ^b   Li, Jiaxing ^c   Ren, Wen Long ^a   Xing, Meng Lei ^a   Sun, Xiao Qiang ^a   Yang, Hai Tao ^a  

^a CHANGZHOU UNIVERSITY   (China)

^b DEZHOU UNIVERSITY   (China)

^c INSTITUTE OF PLASMA PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

[60] FULLERENE; ALKYL AMINES; EFFECTIVE SYNTHESIS; HYPERVALENT IODINE REAGENTS; MEDIATED REACTIONS; REGIO-SELECTIVE;

AMINES; IODINE; SULFUR COMPOUNDS; UREA;

CHEMICAL REACTIONS;

ALIPHATIC AMINE; AMINE; CARBAMIC ACID; CARBAMIC ACID DERIVATIVE; FULLERENE DERIVATIVE; IODINE; REAGENT; SULFONAMIDE; UREA;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; HYPOTHESIS; ISOMER; REACTION TIME; ROOM TEMPERATURE; SYNTHESIS; TEMPERATURE; ULTRAVIOLET RADIATION;

AMINES; FULLERENES; INDICATORS AND REAGENTS; IODINE; MOLECULAR STRUCTURE;

EID: 84890192084     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402079m     Document Type: Article

References (43)

1. Vostrowsky, O.; Hirsch, A. Chem. Rev. 2006, 106, 5191-5207
2. Hummelen, J. C.; Knight, B.; Pavlovich, J.; Gonzalez, R.; Wudl, F. Science 1995, 269, 1554-1556
3. Nuber, B.; Hirsch, A. Chem. Commun. 1996, 1421-1422
4. Nambo, M.; Segawa, Y.; Itami, K. J. Am. Chem. Soc. 2011, 133, 2402-2405
5. Prato, M.; Li, Q. C.; Wudl, F.; Lucchini, V. J. Am. Chem. Soc. 1993, 115, 1148-1150
6. Grosser, T.; Prato, M.; Lucchini, V.; Hirsch, A.; Wudl, F. Angew. Chem., Int. Ed. 1995, 34, 1343-1345
7. Averdung, J.; Mattay, J. Tetrahedron 1996, 52, 5407-5420
8. Shen, C. K.-F.; Yu, H.-H.; Juo, C.-G.; Chien, K.-M.; Her, G.-R.; Luh, T.-Y. Chem. Eur. J. 1997, 3, 744-748
9. Wu, R.; Lu, X.; Zhang, Y.; Zhang, J.; Xiong, W.; Zhu, S. Tetrahedron 2008, 64, 10694-10698
10. Ulmer, L.; Mattay, J. Eur. J. Org. Chem. 2003, 2933-2940
11. Smith, A. B.; Tokuyama, H. Tetrahedron 1996, 52, 5257-5262
12. Averdung, J.; Mattay, J.; Jacobi, D.; Abraham, W. Tetrahedron 1995, 51, 2543-2552
13. Averdung, J.; Luftmann, H.; Mattay, J.; Claus, K.-U.; Abraham, W. Tetrahedron Lett. 1995, 36, 2957-2958
14. Yan, M.; Cai, S. X.; Keana, J. F. W. J. Org. Chem. 1994, 59, 5951-5954
15. Ikuma, N.; Mikie, T.; Doi, Y.; Nakagawa, K.; Kokubo, K.; Oshima, T. Org. Lett. 2012, 14, 6040-6043
16. Minakata, S.; Tsuruoka, R.; Nagamachi, T.; Komatsu, M. Chem. Commun. 2008, 323-325
17. Tsuruoka, R.; Nagamachi, T.; Murakami, Y.; Komatsu, M.; Minakata, S. J. Org. Chem. 2009, 74, 1691-1697
18. Nakahodo, T.; Okada, M.; Morita, H.; Yoshimura, T.; Ishitsuka, M. O.; Tsuchiya, T.; Maeda, Y.; Fujihara, H.; Akasaka, T.; Gao, X.; Nagase, S. Angew. Chem., Int. Ed. 2008, 47, 1298-1300
19. Okada, M.; Nakahodo, T.; Ishitsuka, M. O.; Nikawa, H.; Tsuchiya, T.; Akasaka, T.; Fujie, T.; Yoshimura, T.; Slanina, Z.; Nagase, S. Chem. Asian J. 2010, 6, 416-423
20. Nagamachi, T.; Takeda, Y.; Nakayama, K.; Minakata, S. Chem. Eur. J. 2012, 18, 12035-12045
21. Yang, H.-T.; Ruan, X.-J.; Miao, C.-B.; Xi, H.-T.; Jiang, Y.; Meng, Q.; Sun, X.-Q. Tetrahedron Lett. 2009, 50, 7337-7339
22. Yang, H.-T.; Ruan, X.-J.; Miao, C.-B.; Sun, X.-Q. Tetrahedron Lett. 2010, 51, 6056-6059
23. Yang, H.-T.; Tian, Z.-Y.; Ruan, X.-J.; Zhang, M.; Miao, C.-B.; Sun, X.-Q. Eur. J. Org. Chem. 2012, 4918-4922
24. Yang, H.-T.; Ren, W.-L.; Miao, C.-B.; Dong, C.-P.; Yang, Y.; Xi, H.-T.; Meng, Q.; Jiang, Y.; Sun, X.-Q. J. Org. Chem. 2013, 78, 1163-1170
25. Yang, H.-T.; Liang, X.-C.; Wang, Y.-H.; Yang, Y.; Sun, X.-Q.; Miao, C.-B. Org. Lett. 2013, 15, 4650-4653
26. Boto, A.; Hernández, D.; Hernández, R.; Suárez, E. Org. Lett. 2004, 6, 3785-3788
27. Yuan, X. T.; Liu, K.; Li, C. J. Org. Chem. 2008, 73, 6166-6171
28. Li, W.; Gan, J.; Fan, R. Tetrahedron Lett. 2010, 51, 4275-4277
29. Francisco, C. G.; Herrera, A. J.; Martín, á.; Pérea-Martín, I.; Suárez, E. Tetrahedron Lett. 2007, 48, 6384-6388
30. Martín, A.; Pérea-Martín, I.; Suárez, E. Org. Lett. 2005, 7, 2027-2030
31. Fan, R.; Pu, D.; Wen, F.; Wu, J. J. Org. Chem. 2007, 72, 8994-8997
32. Fan, R.; Li, W.; Pu, D.; Zhang, L. Org. Lett. 2009, 11, 1425-1428
33. Yang, H.-T.; Ren, W.-L.; Dong, C.-P.; Yang, Y.; Sun, X.-Q.; Miao, C.-B. Tetrahedron Lett. 2013, 54, 6799-6803
34. Gündüz, T.; Taştekin, M. Anal. Chim. Acta 1994, 286, 247-251 and references cited therein
35. Zhang, X.; Gan, L.; Huang, S.; Shi, Y. J. Org. Chem. 2004, 69, 5800-5802
36. Yang, H.-T.; Liang, X.-C.; Wang, Y.-H.; Yang, Y.; Sun, X.-Q.; Miao, C.-B. J. Org. Chem. 2013, 10.1021/jo402043p
37. Schick, G.; Hirsch, A.; Mauser, H.; Clark, T. Chem. Eur. J. 1996, 2, 935-943
38. Djojo, F.; Herzog, A.; Lamparth, I.; Hampel, F.; Hirsch, A. Chem. Eur. J. 1996, 2, 1537-1547
39. Ito, H.; Ishiida, Y.; Saigo, K. Tetrahedron Lett. 2005, 46, 8757-8760
40. Ito, H.; Ishida, Y.; Saigo, K. J. Org. Chem. 2006, 71, 4759-4765
41. Gaussian 09, Revision C.01; Gaussian, Inc.: Wallingford, CT.
42. Hirsch, A. Top. Curr. Chem. 1998, 199, 1-65
43. Bühl, M.; Hirsch, A. Chem. Rev. 2001, 101, 1153-1183