title: Reactions of HDDA-Derived Benzynes with Sulfides: Mechanism, Modes, and Three-Component Reactions.
abstract: We report here reactions of alkyl sulfides with benzynes thermally generated by the hexadehydro-Diels-Alder (HDDA) cycloisomerization. The initially produced 1,3-betaine (o-sulfonium/aryl carbanion) undergoes intramolecular proton transfer to generate a more stable S-aryl sulfur ylide. This can react in various manners, including engaging weak acids (HA) in the reaction medium. This can produce transient ion pairs ArSR2(+)A(-) that proceed to the products ArSR + RA. When cyclic sulfides are used, A(-) opens the ring and is incorporated into the product, an outcome that constitutes a versatile, three-component coupling process.
authors.affiliation: Department of Chemistry, University of Minnesota , 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Junhua
authors.initials: J
authors.lastname: Chen
authors.affiliation: Department of Chemistry, University of Minnesota , 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Vignesh
authors.initials: V
authors.lastname: Palani
authors.affiliation: Department of Chemistry, University of Minnesota , 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Thomas R
authors.initials: TR
authors.lastname: Hoye
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D003500:Cyclization; D061565:Cycloaddition Reaction; D007536:Isomerism; D015394:Molecular Structure; D011522:Protons; D013440:Sulfides / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001555:Benzene Derivatives; D011522:Protons; D013440:Sulfides; C524146:benzyne