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Communication | Regular issue | Vol 91, No. 6, 2015, pp.1170-1175
Published online, 15th May, 2015
DOI: 10.3987/COM-15-13227
Preparation of Acylthiophenes by Iron(III) Chloride Catalyzed Reactions of Tris(2-thienyl)stibanes with Acyl Chlorides

Naoki Kakusawa,* Yoshie Nakagawa, Yutarou Toshima, Shuji Yasuike, and Jyoji Kurita

*Faculty of Pharmaceutical Sciences, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan

Abstract

The reactions of tris(2-thienyl)stibanes with various acyl chlorides, using a catalytic amount of iron(III) chloride, afforded 2-acylthiophenes. Iron(III) chloride is presumed to act as a Lewis acid, and the ipso substituent of each 2-thienyl group of tris(2-thienyl)stibane is replaced with an acyl group. The reaction is highly atom-efficient in that all three thiophene rings of tris(2-thienyl)stibane take part in the reaction. The reaction procedure is so simple that it can also be carried out under solvent-free and aerobic conditions.