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An Electroinitiated Cation Chain Reaction: Intramolecular Carbon–Carbon Bond Formation between Thioacetal and Olefin Groups

2008; Wiley; Volume: 47; Issue: 13 Linguagem: Inglês

10.1002/anie.200705748

1521-3773

Kouichi Matsumoto, Shunsuke Fujie, Koji Ueoka, Seiji Suga, Jun‐ichi Yoshida,

Sulfur-Based Synthesis Techniques

Angewandte Chemie International EditionVolume 47, Issue 13 p. 2506-2508 Communication An Electroinitiated Cation Chain Reaction: Intramolecular Carbon–Carbon Bond Formation between Thioacetal and Olefin Groups† Kouichi Matsumoto, Kouichi Matsumoto Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727Search for more papers by this authorShunsuke Fujie, Shunsuke Fujie Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727Search for more papers by this authorKoji Ueoka, Koji Ueoka Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727Search for more papers by this authorSeiji Suga Dr., Seiji Suga Dr. Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727Search for more papers by this authorJun-ichi Yoshida Prof., Jun-ichi Yoshida Prof. yoshida@sbchem.kyoto-u.ac.jp Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727Search for more papers by this author Kouichi Matsumoto, Kouichi Matsumoto Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727Search for more papers by this authorShunsuke Fujie, Shunsuke Fujie Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727Search for more papers by this authorKoji Ueoka, Koji Ueoka Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727Search for more papers by this authorSeiji Suga Dr., Seiji Suga Dr. Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727Search for more papers by this authorJun-ichi Yoshida Prof., Jun-ichi Yoshida Prof. yoshida@sbchem.kyoto-u.ac.jp Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto, 615-8510, Japan, Fax: (+81) 75-383-2727Search for more papers by this author First published: 10 March 2008 https://doi.org/10.1002/anie.200705748Citations: 50 † This work was financially supported in part by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science. We are also grateful to Nippon Shokubai Co. and Nippoh Chemicals Co. for providing sodium tetrakis(pentafluorophenyl)borate as a precursor of Bu4NB(C6F5)4. 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 onFacebookTwitterLinked InRedditWechat Abstract The treatment of an olefinic thioacetal with a catalytic amount of ArS(ArSSAr)+B(C6F5)4−, or the electrolysis of a mixture of an olefinic thioacetal and ArSSAr, gives rise to effective intramolecular carbon–carbon bond formation (see scheme). This transformation opens up great potential for electroinitiated cation chain reactions in organic synthesis. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z705748_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. Volume47, Issue13March 14, 2008Pages 2506-2508 RelatedInformation