This work was supported by the PRESTO program of the Japan Science and Technology Agency (JST), and a Grant-in-Aid for Scientific Research from MEXT and JSPS. J.B. is a recipient of a JSPS Postdoctoral Fellowship. We thank Dr. Kin-ichi Oyama (Nagoya University) for assistance in MALDI-TOF MS analysis, Prof. Yasuhiro Ohki and Prof. Kazuyuki Tatsumi (Nagoya University) for assistance in X-ray crystal structure analysis, and Prof. Atsushi Wakamiya and Prof. Shigehiro Yamaguchi (Nagoya University) for useful discussion and technical assistance. Last but not least, we thank the late Kazuhiko Seki (Nagoya University) for his encouragement.
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Communication
Selective Synthesis of [12]Cycloparaphenylene†
Article first published online: 8 JUL 2009
DOI: 10.1002/anie.200902617
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Takaba, H., Omachi, H., Yamamoto, Y., Bouffard, J. and Itami, K. (2009), Selective Synthesis of [12]Cycloparaphenylene. Angewandte Chemie International Edition, 48: 6112–6116. doi: 10.1002/anie.200902617
- †
Publication History
- Issue published online: 29 JUL 2009
- Article first published online: 8 JUL 2009
- Manuscript Received: 16 MAY 2009
Funded by
- Japan Science and Technology Agency (JST)
- MEXT
- JSPS
Keywords:
- aromaticity;
- cross-coupling;
- cycloparaphenylenes;
- macrocyclization;
- palladium
Graphical Abstract
Tighten your belt: [12]Cycloparaphenylene, the sidewall segment of a carbon nanotube (see picture), has been synthesized in a selective manner through stepwise palladium-catalyzed coupling reactions. The synthesis capitalizes on the ability of the cis-1,4-dihydroxycyclohexane-1,4-diyl unit to attenuate the build-up of strain energy during macrocyclization.