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Note | Regular issue | Vol 81, No. 2, 2010, pp.433-439
Published online, 25th December, 2009
DOI: 10.3987/COM-09-11867
Synthesis of 1-(1-Arylsulfanylalkyl)indoles and 2,2-Bis[1-(1-arylsulfanylalkyl)indol-3-yl]propanes by Acid-Catalyzed Reactions of Indoles with Aryl Vinyl Sulfides

Kazuhiro Kobayashi,* Yuu Shirai, Shuhei Fukamachi, and Hisatoshi Konishi

*Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan


We report a facile synthesis of 1-(1-arylsulfanylalkyl)indoles and 2,2-bis[1-(1-arylsulfanylalkyl)indol-3-yl]propanes under mild conditions. Thus, treatment of 3-substituted indoles with aryl vinyl sulfides in dichloromethane at room temperature in the presence of a catalytic amount of (±)-camphor-10-sulfonic acid yields the former indole derivatives in moderate to fair yields. 3-Nonsubstituted indoles could be transformed into the latter indole derivatives in satisfactory yields on treatment with excess aryl vinyl sulfides in the presence of a catalytic amount of the acid under similar conditions.