3‑Thioaryne Intermediates for the Synthesis of Diverse Thioarenes
journal contributionposted on 25.06.2019, 13:04 by Yu Nakamura, Yoshihiro Miyata, Keisuke Uchida, Suguru Yoshida, Takamitsu Hosoya
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.