title: Drawing from a pool of radicals for the design of selective enyne cyclizations.
abstract: Despite the possibility of intermolecular attack at four different locations, the Bu3Sn-mediated radical cyclization of aromatic enynes is surprisingly selective. The observed reaction path originates from the least stable of the equilibrating pool of isomeric radicals produced by intermolecular Bu3Sn attack at the π-bonds of substrates. The radical pool components are kinetically self-sorted via 5-exo-trig closure, the fastest of the four possible cyclizations. The resulting Sn-substituted indenes are capable of further transformations in reactions with electrophiles.
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University , Tallahassee, Florida 32306, United States, and School of Science, Engineering and Mathematics, Bethune-Cookman University , Daytona Beach, Florida 32114, United States.
authors.forename: Sayantan
authors.initials: S
authors.lastname: Mondal
authors.forename: Rana K
authors.initials: RK
authors.lastname: Mohamed
authors.forename: Mariappan
authors.initials: M
authors.lastname: Manoharan
authors.forename: Hoa
authors.initials: H
authors.lastname: Phan
authors.forename: Igor V
authors.initials: IV
authors.lastname: Alabugin