Construction of Eight-Membered Cyclic Diaryl Sulfides via Domino Reaction of Arynes with Thioaurone Analogues and DFT Study on the Reaction Mechanism.

Eight-membered cyclic and [5,5]-bicyclic sulfides were synthesized via a domino reaction between thioaurone analogues and arynes. Density functional theory calculations were performed to elucidate the reaction mechanism, which involves the elementary steps of the [3 + 2] cycloaddition, 1,2-hydrogen shift, and C(sp2)-S bond cleavage as well as the substituent effect.