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

Arynes were efficiently generated from readily available ortho-sulfinylaryl triflates by the treatment with phenylmagnesium bromide in tetrahydrofuran at -78 degrees 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.