Generation of Arynes Triggered by Sulfoxide–Metal Exchange Reaction of ortho-Sulfinylaryl Triflates

Abstract

Abstract Arynes were efficiently generated from readily available ortho-sulfinylaryl triflates by the treatment with phenylmagnesium bromide in tetrahydrofuran at −78 °C. Aryne generation was initiated by a rapid sulfoxide–metal exchange reaction, followed by the immediate elimination of the ortho-OTf group. Various arynophiles efficiently reacted with arynes generated by this method within 10 min, providing the corresponding adducts in high yields.