Efficient Access to Extended Yagupolskii–Umemoto‐Type Reagents: Triflic Acid Catalyzed Intramolecular Cyclization of <i>ortho</i>‐Ethynylaryltrifluoromethylsulfanes

Angewandte Chemie International EditionVolume 49, Issue 3 p. 572-576 Communication Efficient Access to Extended Yagupolskii–Umemoto-Type Reagents: Triflic Acid Catalyzed Intramolecular Cyclization of ortho-Ethynylaryltrifluoromethylsulfanes† Andrej Matsnev, Andrej Matsnev Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543Search for more papers by this authorShun Noritake, Shun Noritake Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543Search for more papers by this authorYoshinori Nomura, Yoshinori Nomura Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543Search for more papers by this authorEtsuko Tokunaga, Etsuko Tokunaga Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543Search for more papers by this authorShuichi Nakamura Dr., Shuichi Nakamura Dr. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543Search for more papers by this authorNorio Shibata Prof., Norio Shibata Prof. nozshiba@nitech.ac.jp Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543Search for more papers by this author Andrej Matsnev, Andrej Matsnev Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543Search for more papers by this authorShun Noritake, Shun Noritake Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543Search for more papers by this authorYoshinori Nomura, Yoshinori Nomura Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543Search for more papers by this authorEtsuko Tokunaga, Etsuko Tokunaga Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543Search for more papers by this authorShuichi Nakamura Dr., Shuichi Nakamura Dr. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543Search for more papers by this authorNorio Shibata Prof., Norio Shibata Prof. nozshiba@nitech.ac.jp Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543Search for more papers by this author First published: 07 January 2010 https://doi.org/10.1002/anie.200905225Citations: 107 † Support was provided by KAKENHI (21390030). We also thank TOSOH F-TECH INC. We are grateful to Central Glass Co., Ltd. for the gift of trifluoromethanesulfinate. 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 King of the ring: S-(trifluoromethyl)benzo[b]thiophenium salts 1, as analogues of Yagupolskii–Umemoto type reagents, were synthesized by novel triflic acid catalyzed intramolecular cyclization of ortho-ethynylaryltrifluoromethylsulfanes 2. 1 j is especially useful for the electrophilic trifluoromethylation of β-ketoesters and dicyanoalkylidenes. Citing Literature Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_200905225_sm_miscellaneous_information.pdf3.7 MB miscellaneous_information 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. Volume49, Issue3January 12, 2010Pages 572-576 RelatedInformation