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Efficient Access to Extended Yagupolskii–Umemoto-Type Reagents: Triflic Acid Catalyzed Intramolecular Cyclization of ortho-Ethynylaryltrifluoromethylsulfanes

Authors

  • Andrej Matsnev,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543
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  • Shun Noritake,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543
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  • Yoshinori Nomura,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543
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  • Etsuko Tokunaga,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543
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  • Shuichi Nakamura Dr.,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543
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  • Norio Shibata Prof.

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-7543
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  • 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.

Abstract

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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.

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