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Paper | Regular issue | Vol 71, No. 10, 2007, pp.2227-2236
Published online, 20th July, 2007
DOI: 10.3987/COM-07-11138
Preparation of 1,4-Bis(2-ethynyl-3-thienyl)benzenes as Versatile Spacers for Connection of Heterocycles

Kozo Toyota,* Yoichi Goto, Kazuyuki Okada, and Noboru Morita

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

Abstract

Iodination of 1,4-di(3-thienyl)benzene gave 1,4-bis(2-iodo-3-thienyl)benzene, which was converted to 1,4-bis(2-ethynyl-3-thienyl)benzene. Novel 1,4-bis[2-(pyridylethynyl)-3-thienyl]benzene ligands containing the bis(ethynylthienyl)benzene spacer were prepared by Sonogashira reaction. Advantage of the spacer was demonstrated by introducing functionalized alkyl groups to the 5-position of the thiophene ring of 1,4-bis[2-(trialkylsilylethynyl)-3-thienyl]benzene.