title: Regioselective One-Pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates.
abstract: We developed the novel one-pot synthetic method of substituted triptycenes by the reaction of ynolates and arynes. This four-step process involves three cycloadditions and electrocyclic ring opening of the strained Dewar anthracene. Each of the three related but structurally distinct classes of nucleophiles (ynolate, enolate, and anthracenolate) reacts with o-benzyne in the same predictable manner controlled by chelation and negative hyperconjugation. The resulting functionalized C3-symmetrical triptycenes hold promise in the design of functional materials.
authors.affiliation: Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580, Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Umezu
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL, 32310, USA.
authors.forename: Gabriel
authors.initials: G
authors.lastname: Dos Passos Gomes
authors.affiliation: Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580, Japan.
authors.forename: Tatsuro
authors.initials: T
authors.lastname: Yoshinaga
authors.affiliation: Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580, Japan.
authors.forename: Mikei
authors.initials: M
authors.lastname: Sakae
authors.affiliation: Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580, Japan.
authors.forename: Kenji
authors.initials: K
authors.lastname: Matsumoto
authors.affiliation: Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580, Japan.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Iwata
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL, 32310, USA.
authors.forename: Igor
authors.initials: I
authors.lastname: Alabugin
authors.affiliation: Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580, Japan.
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Shindo
keywords: aryne; directing effect; hyperconjugation; triptycene; ynolate