title: Synthesis of disubstituted dithioethers: tert-butoxide promoted elimination/ring opening of 1,3-dithianes followed by palladium-catalyzed C-S bond formation.
abstract: We report the tandem base-promoted elimination/ring-opening of 2-benzyl-1,3-dithianes with subsequent cross coupling of the pendent thiol with a range of aryl bromides. A simple Pd(OAc)2/Xantphos catalyst system affects this new reaction and is compatible with a wide range of functional groups, including heteroaromatic coupling partners. The transformation proceeds in good to excellent yields (69-99%) and exhibits strong stereoselectivity, forming the E-alkene as the major diastereomer. This new methodology provides access to nonsymmetric propylene styryl/aryl dithioethers, a previously undisclosed motif.
authors.affiliation: Department of Chemistry, Bryn Mawr College, 101 N. Merion Avenue, Bryn Mawr, Pennsylvania 19010, United States.
authors.forename: Nissa
authors.initials: N
authors.lastname: Abidi
authors.affiliation: Department of Chemistry, Bryn Mawr College, 101 N. Merion Avenue, Bryn Mawr, Pennsylvania 19010, United States.
authors.forename: Jason R
authors.initials: JR
authors.lastname: Schmink