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Synfacts 2009(11): 1216-1216  
DOI: 10.1055/s-0029-1218087
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Functionalization of Perylene through C-H Bond Activation

Contributor(s): Timothy M. Swager, Jason R. Cox
S. Nakazono, Y. Imazaki, H. Yoo, J. Yang, T. Sasamori, N. Tokitoh, T. Cédric, H. Kageyama*, D. Kim*, H. Shinokubo*, A. Osuka*
Kyoto University, Nagoya University, Japan and Yonsei University, Seoul, Korea
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

The regioselective functionalization of perylene bisimides using the Murai-Chatani-Kakiuchi protocol is described. The authors recognized that the carbonyl groups could be used to activate the C-H bonds of the 2, 5, 8 and 11 positions for functionalization. This simple procedure provides alkylated perylene bisimides in moderate to good yields (45-95%) with the caveat that only a narrow range of R groups can be introduced.