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Angewandte Chemie International EditionVolume 47, Issue 21 p. 4019-4022 Communication Fluorescent Naphthyl- and Anthrylazoles from the Catalytic Coupling of Phenylazoles with Internal Alkynes through the Cleavage of Multiple CH Bonds† Nobuyoshi Umeda, Nobuyoshi Umeda Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-7362 http://www.chem.eng.osaka-u.ac.jp/∼miura-lab/index-Eng.htmSearch for more papers by this authorHayato Tsurugi Dr., Hayato Tsurugi Dr. Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-7362 http://www.chem.eng.osaka-u.ac.jp/∼miura-lab/index-Eng.htmSearch for more papers by this authorTetsuya Satoh Prof. Dr., Tetsuya Satoh Prof. Dr. [email protected] Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-7362 http://www.chem.eng.osaka-u.ac.jp/∼miura-lab/index-Eng.htmSearch for more papers by this authorMasahiro Miura Prof. Dr., Masahiro Miura Prof. Dr. [email protected] Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-7362 http://www.chem.eng.osaka-u.ac.jp/∼miura-lab/index-Eng.htmSearch for more papers by this author Nobuyoshi Umeda, Nobuyoshi Umeda Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-7362 http://www.chem.eng.osaka-u.ac.jp/∼miura-lab/index-Eng.htmSearch for more papers by this authorHayato Tsurugi Dr., Hayato Tsurugi Dr. Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-7362 http://www.chem.eng.osaka-u.ac.jp/∼miura-lab/index-Eng.htmSearch for more papers by this authorTetsuya Satoh Prof. Dr., Tetsuya Satoh Prof. Dr. [email protected] Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-7362 http://www.chem.eng.osaka-u.ac.jp/∼miura-lab/index-Eng.htmSearch for more papers by this authorMasahiro Miura Prof. Dr., Masahiro Miura Prof. Dr. [email protected] Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-7362 http://www.chem.eng.osaka-u.ac.jp/∼miura-lab/index-Eng.htmSearch for more papers by this author First published: 06 May 2008 https://doi.org/10.1002/anie.200800924Citations: 404 † We thank Prof. Dr. N. Tohnai, Osaka University, for fluorescence quantum efficiency measurements and helpful discussions. This work was partly supported by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science, and Technology (Japan) and the Sumitomo Foundation. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Bright light rings: The direct coupling of phenylazoles with an internal alkyne proceeds efficiently in the presence of a rhodium catalyst and a copper oxidant to selectively give either the 1-naphthyl- or 1-anthrylazole derivatives through the cleavage of multiple CH bonds (see scheme; 1-naphthylazole derivative not shown). Some of the products exhibit intense fluorescence in the solid state. Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z800924_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1Selected reviews: 1aJ. E. Anthony, Angew. Chem. 2008, 120, 460; Angew. Chem. 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