2,3-Disubstituted 6,7-furanobenzynes were efficiently generated from ortho-iodoaryl triflate-type precursors using a silyl-methyl Grignard reagent as the activator. The reactions between 6,7-furanobenzynes and unsymmetrical arynophiles proceeded in a highly regioselective manner. Since a variety of precursors were easily synthesizable from readily available 2,3-disubstituted 6-hydroxybenzofurans, this method enabled facile synthesis of a wide range of multisubstituted benzofurans, including pi-extended molecules.