Copper-catalyzed formal [4 + 2] annulation between alkyne and fullerene bromide

Journal of the American Chemical Society

Volumn 132, Issue 35, 2010, Pages 12234-12236

  Xiao, Zuo ^a   Matsuo, Yutaka ^a,b   Nakamura, Eiichi ^a,b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

[60] FULLERENE; ANNULATION REACTIONS; ARYL ACETYLENES; ARYL GROUP; AXIAL CHIRALITY; CH-BOND ACTIVATION; COPPER-CATALYZED REACTIONS; RADICAL MECHANISM; RESTRICTED ROTATIONS;

ACETYLENE; BROMINE COMPOUNDS; CATALYSIS; FULLERENES; STEREOCHEMISTRY;

COPPER;

ACETYLENE DERIVATIVE; ALKYNE; ARSENIC; BROMIDE; CARBON; COPPER; COPPER COMPLEX; DEUTERIUM; DIHYDRONAPHTHALENE; FULLERENE; HYDROGEN; NAPHTHALENE DERIVATIVE; PHENYLACETYLENE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; COLUMN CHROMATOGRAPHY; CRYSTAL STRUCTURE; HYDROGEN BOND; ISOTOPE LABELING; REACTION ANALYSIS; ROOM TEMPERATURE; STRUCTURE ANALYSIS;

ALKYNES; BROMIDES; CATALYSIS; COPPER; CYCLIZATION; FULLERENES; MOLECULAR STRUCTURE; NAPHTHALENES; STEREOISOMERISM;

EID: 77956254541     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1056399     Document Type: Article

References (24)

1. Hirsch, A. and Brettreich, M. Fullerenes: Chemistry and Reactions; Wiley-VCH: Weinheim, Germany, 2005.
2. Nambo, M., Noyori, R., and Itami, K. J. Am. Chem. Soc. 2007, 129, 8080
3. Mori, S., Nambo, M., Chi, L.-C., Bouffard, J., and Itami, K. Org. Lett. 2008, 10, 4609
4. Nambo, M. and Itami, K. Chem.-Eur. J. 2009, 15, 4760
5. Zhu, B. and Wang, G. W. J. Org. Chem. 2009, 74, 4426
6. Zhu, B. and Wang, G. W. Org. Lett. 2009, 11, 4334
7. Filippone, S., Maroto, E. E., Martiěn-Domenech, Aě., Suarez, M., and Martiěn, N. Nat. Chem. 2009, 1, 578
8. Matsuo, Y., Kuninobu, Y., Muramatsu, A., Sawamura, M., and Nakamura, E. Organometallics 2008, 27, 3403
9. 60 was also achieved in high yields; see the Supporting Information
10. Sawamura, M., Iikura, H., and Nakamura, E. J. Am. Chem. Soc. 1996, 118, 12850
11. Matsuo, Y., Muramatsu, A., Tahara, K., Koide, M., and Nakamura, E. Org. Synth. 2006, 83, 80
12. Matsuo, Y. and Nakamura, E. Chem. Rev. 2008, 108, 3016
13. Bottari, G., Torre, G., Guldi, D. M., and Torres, T. Chem. Rev. [Online early access]. DOI: 10.1021/cr900254z. Published Online: April 5, 2010.
14. Mishra, A., Ma, C. Q., and Bauerle, P. Chem. Rev. 2009, 109, 1141
15. Birkett, P. R., Taylor, R., Wachter, N. K., Carano, M., Paolucci, F., Roffia, S., and Zerbetto, F. J. Am. Chem. Soc. 2000, 122, 4209
16. Clavaguera, S., Khan, S. I., and Rubin, Y. Org. Lett. 2009, 11, 1389
17. Hu, X. Q., Jiang, Z. P., Jia, Z. S., Huang, S. H., Yang, X. B., Li, Y. L., Gan, L. B., Zhang, S. W., and Zhu, D. B. Chem.-Eur. J. 2007, 13, 1129
18. Isobe, H., Tanaka, T., Nakanishi, W., Lemiěgre, L., and Nakamura, E. J. Org. Chem. 2005, 70, 4826
19. Nakamura, Y., Suzuki, M., Kyoji, O., Konno, T., and Nishimura, J. J. Org. Chem. 2005, 70, 8472
20. 5Br and 4-bromostyrene catalyzed by CuI afforded the annulated product in 82% yield after 24 h. Related results will be published in due course.
21. Yamada, M., Rivera-Fuentes, P., Schweizer, W. B., and Diederich, F. Angew. Chem., Int. Ed. 2010, 49, 3532
22. Meca, L., Řeha, D., and Havlas, Z. J. Org. Chem. 2003, 68, 5677
23. Matyjaszewski, K. and Xia, J. Chem. Rev. 2001, 101, 2921
24. Clark, A. J. Chem. Soc. Rev. 2002, 31, 1