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3-Thioaryne Intermediates for the Synthesis of Diverse Thioarenes
Yu Nakamura1, Yoshihiro Miyata1, Keisuke Uchida1
1Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering , Tokyo Medical and Dental University (TMDU) , 2-3-10 Kanda-Surugadai , Chiyoda-ku, Tokyo 101-0062 , Japan.
Abstract:
The synthetic utility of 3-thioaryne intermediates has been demonstrated through an aryne relay approach. The efficient synthesis of o-silylaryl triflate-type 3-thioaryne precursors has been achieved by the regioselective silylthiolation of 3-(triflyloxy)arynes with silyl sulfides. Various 3-thioarynes were successfully generated from these precursors and reacted with various arynophiles to afford diverse multisubstituted aryl sulfides. Further derivatizations of the products enabled easy access to the novel sulfur-containing π-extended heterocycles, which demonstrates the utility of this method.
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