Synthesis and racemization process of chiral carbon nanorings: A step toward the chemical synthesis of chiral carbon nanotubes

Organic Letters

Volumn 13, Issue 9, 2011, Pages 2480-2483

  Omachi, Haruka ^a   Segawa, Yasutomo ^a   Itami, Kenichiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79955594751     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200730m     Document Type: Article

References (35)

1. Fort, E. H.; Donovan, P. M.; Scott, L. T. J. Am. Chem. Soc. 2009, 131, 16006
2. Fort, E. H.; Scott, L. T. Angew. Chem., Int. Ed. 2010, 49, 6626
3. Fort, E. H.; Scott, L. T. J. Mater. Chem. 2011, 21, 1373
4. Smalley, R. E.; Li, Y.; Moore, V. C.; Price, B. K.; Colorado, R., Jr.; Schmidt, H. K.; Hauge, R. H.; Barron, A. R.; Tour, J. M. J. Am. Chem. Soc. 2006, 128, 15824
5. Yu, X.; Zhang, J.; Choi, W.; Choi, J.-Y.; Kim, J. M.; Gan, L.; Liu, Z. Nano Lett. 2010, 10, 3343
6. Jasti, R.; Bertozzi, C. R. Chem. Phys. Lett. 2010, 494, 1
7. Bodwell, G. J. Nat. Nanotechnol. 2010, 5, 103
8. Reviews on aromatic carbon nanorings and belts: Yao, T.; Yu, H.; Vermeij, R. J.; Bodwell, G. J. Pure Appl. Chem. 2008, 80, 533
9. Tahara, K.; Tobe, Y. Chem. Rev. 2006, 106, 5274
10. Kawase, T.; Kurata, H. Chem. Rev. 2006, 106, 5250
11. Scott, L. T. Angew. Chem., Int. Ed. 2003, 42, 4133
12. Frank, S.; Poncharal, P.; Wang, Z. L.; de Heer, W. A. Science 1998, 280, 1744
13. Wu, Z. C.; Chen, Z. H.; Du, X.; Logan, J. M.; Sippel, J.; Nikolou, M.; Kamaras, K.; Reynolds, J. R.; Tanner, D. B.; Hebard, A. F.; Rinzler, A. G. Science 2004, 305, 1273
14. Zhou, X. J.; Park, J. Y.; Huang, S. M.; Liu, J.; McEuen, P. L. Phys. Rev. Lett. 2005, 95, 146805
15. Pd-catalyzed selective synthesis of [12]CPP: Takaba, H.; Omachi, H.; Yamamoto, Y.; Bouffard, J.; Itami, K. Angew. Chem., Int. Ed. 2009, 48, 6112
16. Modular and size-selective synthesis of [ n ]CPPs (demonstrated for n = 14-16): Omachi, H.; Matsuura, S.; Segawa, Y.; Itami, K. Angew. Chem., Int. Ed. 2010, 49, 10202
17. Ni-mediated synthesis and X-ray crystal structure of [12]CPP: Segawa, Y.; Miyamoto, S.; Omachi, H.; Matsuura, S.; Ŝenel, P.; Sasamori, T.; Tokitoh, N.; Itami, K. Angew. Chem., Int. Ed. 2011, 50, 3244
18. Ni-mediated synthesis and X-ray crystal structure of [9]CPP: Segawa, Y.; Ŝenel, P.; Matsuura, S.; Omachi, H.; Itami, K. Chem. Lett. 2011, 40, 423
19. DFT calculation on the structures and strain energies of [ n ]CPPs: Segawa, Y.; Omachi, H.; Itami, K. Org. Lett. 2010, 12, 2262
20. For other CPP syntheses, see: Jasti, R.; Bhattacharjee, J.; Neaton, J. B.; Bertozzi, C. R. J. Am. Chem. Soc. 2008, 130, 17646
21. Yamago, S.; Watanabe, Y.; Iwamoto, T. Angew. Chem., Int. Ed. 2010, 49, 757
22. Previous reports on the synthesis of fully conjugated macrocycles related to CPPs. Picotubes: Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417
23. Kammermeier, S.; Jones, P. G.; Herges, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 2200
24. Tsuji, T.; Okuyama, M.; Ohkita, M.; Imai, T.; Suzuki, T. Chem. Commun. 1997, 2151 Cyclothiophenes: Kroümer, J.; Rios-Carreras, I.; Fuhrmann, G.; Musch, C.; Wunderlin, M.; Debaerdemaeker, T.; Mena-Osteritz, E.; Baüuerle, P. Angew. Chem., Int. Ed. 2000, 39, 3481
25. Zhang, F.; Goütz, G.; Winkler, H. D. F.; Schalley, C. A.; Baüuerle, P. Angew. Chem., Int. Ed. 2009, 48, 6632 Cyclopyrroles: Seidel, D.; Lynch, V.; Sessler, J. L. Angew. Chem., Int. Ed. 2002, 41, 1422
26. Koühler, T.; Seidel, D.; Lynch, V.; Arp, F. O.; Ou, Z.; Kadish, K. M.; Sessler, J. L. J. Am. Chem. Soc. 2003, 125, 6872 Cyclocarbazoles: Jung, S.-H.; Pisula, W.; Rouhanipour, A.; Raüder, H. J.; Jacob, J.; Muüllen, K. Angew. Chem., Int. Ed. 2006, 45, 4685 Acetylene-inserted CPPs: Kawase, T.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2664
27. Srinivasan, M.; Sankararaman, S.; Hopf, H.; Varghese, B. Eur. J. Org. Chem. 2003, 660
28. For reviews on the synthesis of shape-persistent macrocycles, see: Hoüger, S. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 2685
29. Grave, C.; Schluüter, A. D. Eur. J. Org. Chem. 2002, 3075
30. Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508
31. dppf = 1,1′-bis(diphenylphosphino)ferrocene. dba = dibenzylideneacetone. X-Phos = 2-dicyclohexylphosphino-2′,4′, 6′-triisopropylbiphenyl.
32. Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461
33. The racemization processes of chiral carbon nanorings having even-number benzene units are slightly different from that of 1. See the Supporting Information for details.
34. A homodesmotic reaction is a reaction in which reactants and products contain equal numbers of carbon atoms in corresponding states of hybridization. Moreover, there is matching of the carbon-hydrogen bonds in terms of the number of hydrogen atoms joined to the individual carbon atoms. Minkin, V. I. Pure Appl. Chem. 1999, 71, 1919
35. George, P.; Trachtman, M.; Bock, C. W.; Brett, A. M. Tetrahedron 1976, 32, 317