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Paper | Special issue | Vol 82, No. 1, 2010, pp.689-697
Published online, 5th July, 2010
DOI: 10.3987/COM-10-S(E)44
Synthesis of Bis(benzo[b]thiophenyl)methanes by Gold-Catalyzed Double Carbothiolation

Itaru Nakamura,* Masashi Okamoto, Takuma Sato, and Masahiro Terada

*Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan

Abstract

Gold-catalyzed double cyclization of bis(2-alkynylphenylthio)acetals (1) produced bis(benzo[b]thiophen-3-yl)methanes (2) in good to excellent yields with high catalyst turnover number. For example, the reaction of (phenylmethylene)bis((2-(phenylethynyl)phenyl)sulfane) (1b) in the presence of 1 mol% of AuCl in toluene at 25 °C for 1 hour gave 3,3'-(phenylmethylene)bis(2-phenylbenzo[b]thiophene) (2b) in 97% isolated yield. The present reaction proceeded through two successive intramolecular carbon-sulfur bond addition reactions, or the so-called carbothiolation.