title: Synthesis of sulfur-containing heterocycles through oxidative carbon-hydrogen bond functionalization.
abstract: Vinyl sulfides react rapidly and efficiently with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form α,β-unsaturated thiocarbenium ions through oxidative carbon-hydrogen bond cleavage. These electrophiles couple with appended π-nucleophiles to yield sulfur-containing heterocycles through carbon-carbon bond formation. Several nucleophiles are compatible with the procedure, and the reactions generally proceed through readily predictable transition states.
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
authors.forename: Yubo
authors.initials: Y
authors.lastname: Cui
authors.forename: Paul E
authors.initials: PE
authors.lastname: Floreancig
mesh_terms: D016227:Benzoquinones / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D016227:Benzoquinones; D013457:Sulfur Compounds; D014753:Vinyl Compounds; C000928:dichlorodicyanobenzoquinone