A facile and efficient preparation of pillararenes and a pillarquinone

Angewandte Chemie - International Edition

Volumn 48, Issue 51, 2009, Pages 9721-9723

  Cao, Derong ^a   Kou, Yuhui ^a   Liang, Jianquan ^a   Chen, Zhizhao ^a   Wang, Lingyun ^a   Meier, Herbert ^b  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Arenes; Cyclooligomers; Host guest chemistry; Ipso alkylation; Quinones

Indexed keywords

ARENES; BENZENE RING; EFFICIENT SYNTHESIS; HOSTGUEST CHEMISTRY; OXIDATION PRODUCTS;

ALKYLATION; BENZENE; HYDROCARBONS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

EID: 71949119271     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200904765     Document Type: Article

References (27)

1. a) G. S. Ananchenko, I. L. Moudrakovski, A. W. Coleman, J. A. Ripmeester, Angew. Chem. 2008, 120, 5698;
2. Angew. Chem. Int. Ed. 2008, 47, 5616;
3. b) S. J. Dalgarno, J. Tian, J. E. Warren, T. E. Clark, M. Makha, C. L. Rastoncand, J. L. Atwood, Chem. Commun. 2007, 4848.
4. a) V. G. Organo, A. V. Leontiev, V. Sgarlata, H. V. Rasika Dias, D. M. Rudkevich, Angew. Chem. 2005, 117, 3103;
5. Angew. Chem. Int. Ed. 2005, 44, 3043;
6. b) T. Ogoshi, T. A. Yamagishi, Y. Nakamoto, Chem. Commun. 2007, 4776.
7. D. M. Homden, C. Redshaw, Chem. Rev. 2008, 108, 5086.
8. R. Zadmard, T. Schrader, Angew. Chem. 2006, 118, 2769;
9. Angew. Chem. Int. Ed. 2006, 45, 2703.
10. a) J. L. Atwood, G. A. Koutsantonis, C. L. Raston, Nature 1994, 368, 229;
11. b) J. S. Wang, C. D. Gutsche, J. Org. Chem. 2000, 65, 6273;
12. c) D B. Qin, X. S. Zeng, Q. S. Li, F. B. Xu, H. B. Song, Z. Z. Zhang, Chem. Commun. 2007, 147;
13. d) S. Q. Liu, D. X. Wang, Q. Y. Zheng, M. X. Wang, Chem. Commun. 2007, 3856.
14. a) P. A. Gale, P. J. Anzenbacher, J. L. Sessler, Coord. Chem. Rev. 2001, 222, 57;
15. b) R. Nishiyabu, P. Anzenbacher, Org. Lett. 2006, 8, 359.
16. a) N. Morohashi, F. Narumi, N. Iki, T. Hattori, S. Miyano, Chem. Rev. 2006, 106, 5291;
17. b) D. Buccella, G. Parkin, J. Am. Chem. Soc. 2008, 130, 8617.
18. a) C. D. Gutsche, B. Dhawan, K. H. No, R. Muthukrishnan, J. Am. Chem. Soc. 1981, 103, 3782;
19. b) A. Ikeda, M. Yoshimura, H. Udzu, C. Fukuhara, S. Shinkai, J Am. Chem. Soc. 1999, 121, 4296;
20. c) B. Masci, J Org. Chem. 2001, 66, 1497;
21. d) B. Masci, S. L. Mortera, D. Persiani, P. Thury, Org. Lett. 2006, 8, 4405.
22. T. Ogoshi, S. Kanai, S. Fujinami, T.-A. Yamagishi, Y. Nakamoto, J Am. Chem. Soc. 2008, 130, 5022.
23. 5 (R = OTf and R = C=CPh), which were obtained in overall yields below 2%. See T. Ogoshi, K. Umeda, T.-A. Yamagishi, Y. Nakamoto, Chem. Commun. 2009, 4874.
24. R. Rathore, J. K. Kochi, J. Org. Chem. 1995, 60, 7479.
25. G W Gribble, C. F. Nutaitis, Tetrahedron Lett. 1985, 26, 6023.
26. See for example: H.-J. Schneider, Angew. Chem. 2009, 121, 3982-4036;
27. Angew. Chem. Int. Ed. 2009, 48, 3924-3977.