title: Palladium-Catalyzed Synthesis of Aryl Vinyl Sulfides via 1,3-Oxathiolanes As Vinyl Sulfide Surrogates.
abstract: A nontraditional approach to synthesizing aryl vinyl sulfides is described. 2,2-Diphenyl-1,3-oxathiolane slowly liberates a vinyl sulfide anion under basic conditions. Using a Pd/Xantphos catalyst system to activate a wide range of aryl bromides, this transient sulfide species can be effectively trapped and fed into a traditional Pd0/PdIIcatalytic cycle. Scope and limitations of the methodology are presented along with significant discussion of a competitive C-S bond activation by this catalyst system.
authors.affiliation: Department of Chemistry, Bryn Mawr College , 101 North Merion Avenue, Bryn Mawr, Pennsylvania 19010-2899, United States.
authors.forename: Jason R
authors.identifier: 0000-0002-3347-0960
authors.initials: JR
authors.lastname: Schmink
authors.affiliation: Department of Chemistry, Bryn Mawr College , 101 North Merion Avenue, Bryn Mawr, Pennsylvania 19010-2899, United States.
authors.forename: Summer A Baker
authors.initials: SA
authors.lastname: Dockrey
authors.affiliation: Department of Chemistry, Bryn Mawr College , 101 North Merion Avenue, Bryn Mawr, Pennsylvania 19010-2899, United States.
authors.forename: Tianyi
authors.initials: T
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, Bryn Mawr College , 101 North Merion Avenue, Bryn Mawr, Pennsylvania 19010-2899, United States.
authors.forename: Naomi
authors.initials: N
authors.lastname: Chebet
authors.affiliation: Department of Chemistry, Bryn Mawr College , 101 North Merion Avenue, Bryn Mawr, Pennsylvania 19010-2899, United States.
authors.forename: Alexis
authors.initials: A
authors.lastname: van Venrooy
authors.affiliation: Department of Chemistry, Bryn Mawr College , 101 North Merion Avenue, Bryn Mawr, Pennsylvania 19010-2899, United States.
authors.forename: Mary
authors.initials: M
authors.lastname: Sexton
authors.affiliation: Department of Chemistry, Bryn Mawr College , 101 North Merion Avenue, Bryn Mawr, Pennsylvania 19010-2899, United States.
authors.forename: Sarah I
authors.initials: SI
authors.lastname: Lew
authors.affiliation: Department of Chemistry, Bryn Mawr College , 101 North Merion Avenue, Bryn Mawr, Pennsylvania 19010-2899, United States.
authors.forename: Steffany
authors.initials: S
authors.lastname: Chou
authors.affiliation: Department of Chemistry, Bryn Mawr College , 101 North Merion Avenue, Bryn Mawr, Pennsylvania 19010-2899, United States.
authors.forename: Ami
authors.initials: A
authors.lastname: Okazaki