A Facile and Efficient Preparation of Pillararenes and a Pillarquinone†
Derong Cao Prof. Dr.
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (China), Fax: (+86) 20-8711-0245
Search for more papers by this authorYuhui Kou
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (China), Fax: (+86) 20-8711-0245
Search for more papers by this authorJianquan Liang
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (China), Fax: (+86) 20-8711-0245
Search for more papers by this authorZhizhao Chen
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (China), Fax: (+86) 20-8711-0245
Search for more papers by this authorLingyun Wang
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (China), Fax: (+86) 20-8711-0245
Search for more papers by this authorHerbert Meier Prof. Dr.
Institute für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55099 Mainz (Germany)
Search for more papers by this authorDerong Cao Prof. Dr.
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (China), Fax: (+86) 20-8711-0245
Search for more papers by this authorYuhui Kou
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (China), Fax: (+86) 20-8711-0245
Search for more papers by this authorJianquan Liang
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (China), Fax: (+86) 20-8711-0245
Search for more papers by this authorZhizhao Chen
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (China), Fax: (+86) 20-8711-0245
Search for more papers by this authorLingyun Wang
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (China), Fax: (+86) 20-8711-0245
Search for more papers by this authorHerbert Meier Prof. Dr.
Institute für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55099 Mainz (Germany)
Search for more papers by this authorThis work is supported by the National Natural Science Foundation of China (20572111), the Science and Technology Planning Project of Guangdong Province (2007A010500011), and the Research Fund for the Doctoral Program of Higher Education of China (20060561024).
Graphical Abstract
References
- 1
- 1aG. S. Ananchenko, I. L. Moudrakovski, A. W. Coleman, J. A. Ripmeester, Angew. Chem. 2008, 120, 5698;
10.1002/ange.200800071 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 5616;
- 1bS. J. Dalgarno, J. Tian, J. E. Warren, T. E. Clark, M. Makha, C. L. Rastoncand, J. L. Atwood, Chem. Commun. 2007, 4848.
- 2
- 2aV. G. Organo, A. V. Leontiev, V. Sgarlata, H. V. Rasika Dias, D. M. Rudkevich, Angew. Chem. 2005, 117, 3103;
10.1002/ange.200500057 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 3043;
- 2bT. Ogoshi, T. A. Yamagishi, Y. Nakamoto, Chem. Commun. 2007, 4776.
- 3D. M. Homden, C. Redshaw, Chem. Rev. 2008, 108, 5086.
- 4R. Zadmard, T. Schrader, Angew. Chem. 2006, 118, 2769;
10.1002/ange.200502946 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 2703.
- 5
- 5aJ. L. Atwood, G. A. Koutsantonis, C. L. Raston, Nature 1994, 368, 229;
- 5bJ. S. Wang, C. D. Gutsche, J. Org. Chem. 2000, 65, 6273;
- 5cD. B. Qin, X. S. Zeng, Q. S. Li, F. B. Xu, H. B. Song, Z. Z. Zhang, Chem. Commun. 2007, 147;
- 5dS. Q. Liu, D. X. Wang, Q. Y. Zheng, M. X. Wang, Chem. Commun. 2007, 3856.
- 6
- 6aP. A. Gale, P. J. Anzenbacher, J. L. Sessler, Coord. Chem. Rev. 2001, 222, 57;
- 6bR. Nishiyabu, P. Anzenbacher, Org. Lett. 2006, 8, 359.
- 7
- 7aN. Morohashi, F. Narumi, N. Iki, T. Hattori, S. Miyano, Chem. Rev. 2006, 106, 5291;
- 7bD. Buccella, G. Parkin, J. Am. Chem. Soc. 2008, 130, 8617.
- 8
- 8aC. D. Gutsche, B. Dhawan, K. H. No, R. Muthukrishnan, J. Am. Chem. Soc. 1981, 103, 3782;
- 8bA. Ikeda, M. Yoshimura, H. Udzu, C. Fukuhara, S. Shinkai, J. Am. Chem. Soc. 1999, 121, 4296;
- 8cB. Masci, J. Org. Chem. 2001, 66, 1497;
- 8dB. Masci, S. L. Mortera, D. Persiani, P. Thury, Org. Lett. 2006, 8, 4405.
- 9T. Ogoshi, S. Kanai, S. Fujinami, T.-A. Yamagishi, Y. Nakamoto, J. Am. Chem. Soc. 2008, 130, 5022.
- 10After submission of this paper, we noticed two additional compounds 25 (R=OTf and R=CCPh), which were obtained in overall yields below 2 %. See T. Ogoshi, K. Umeda, T.-A. Yamagishi, Y. Nakamoto, Chem. Commun. 2009, 4874.
- 11R. Rathore, J. K. Kochi, J. Org. Chem. 1995, 60, 7479.
- 12G. W. Gribble, C. F. Nutaitis, Tetrahedron Lett. 1985, 26, 6023.
- 13See for example: H.-J. Schneider, Angew. Chem. 2009, 121, 3982–4036;
10.1002/ange.200802947 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 3924–3977.