Study Of Aryne Reactions With Sulfides

Aromatic compounds and their derivatives with heterosubstituted groups are ubiquitous in many natural products,drug molecules as well as organic functional materials.Arynes with highly reactive carbon-carbon triple bond could display various reactivities toward these molecules.Due to the unique nature of sulfur atom,the thioether has been often employed as nucleophiles in the organic reactions.Enlightened by the reaction between arynes and sulfur containing compounds,we herein developed two novel aryne reactions involve key sulfonium intermediate.Using Kobayashi aryne precursor and allyl sulfides,we accomplished the Stevens rearrangement and synthesized a variety of allyl sulfide products.The three-component reaction of Kobayashi aryne precursor,cyclic sulfides and nucleophiles with active hydrogen atom provided a diverse range of ring opening products.Notably,these two protocols generate C-S and C-C bonds simultaneously.Both of the two protocols gave the thioether products in high yields and demonstrated large substrate scope.It showed great applicability.Finally,studies on product functionalization and nucleophile scale indicate that our protocols should be of great utilities.