Theoretical Investigation of Regioselectivity in the Rh-Catalyzed Coupling Reaction of 3-Phenylthiophene with Styrene

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  • HAYASHI Yoshihiro
    Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-E4-6 Ookayama, Meguro-ku, Tokyo, 152-8552, Japan
  • SATOH Tetsuya
    Department of Chemistry, Graduate School of Science, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka, 558-8585, Japan
  • MIURA Masahiro
    Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka, 565-0871, Japan
  • KAWAUCHI Susumu
    Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-E4-6 Ookayama, Meguro-ku, Tokyo, 152-8552, Japan

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Other Title
  • Rh触媒による3-フェニルチオフェンとスチレンのカップリング反応における位置選択性の理論的研究

Abstract

<p>Regioselectivity in the Rh-catalyzed coupling reaction of 3-phenylthiophene with styrene was investigated by quantum chemistry calculations. The coupling reaction experimentally reported that styrene is selectively coupled to the phenyl group of the phenylthiophene. Results of the reaction path search and the natural bond orbital analysis indicate that the coupling position is determined by the preference of the styrene insertion into the 5-membered rhodacycle intermediate, which is produced by the double C–H bond cleavage of 3-phenylthiophene in presence of the Rh-catalyst.</p>

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