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.

JOURNAL： Organic Letters

TITLE：3-Thioaryne Intermediates for the Synthesis of Diverse Thioarenes

DOI：https://doi.org/10.1021/acs.orglett.9b01862

Takamitsu HOSOYA, Professor
Department of Chemical Bioscience,
Institute of Biomaterials and Bioengineering,
Tokyo Medical and Dental University(TMDU)
E-mail：thosoya.cb(at)tmd.ac.jp


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