Title: Regioselective One-Pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates.
Authors: Umezu, Satoshi; dos Passos Gomes, Gabriel; Yoshinaga, Tatsuro; Sakae, Mikei; Matsumoto, Kenji; Iwata, Takayuki; Alabugin, Igor; Shindo, Mitsuru
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.
Subjects: REGIOSELECTIVITY (Chemistry); TRIPTYCENES; RING formation (Chemistry); ELECTROCYCLIC reactions (Chemistry); NUCLEOPHILES; CHELATION
Publication: Angewandte Chemie, 2017, Vol 129, Issue 5, p1318
ISSN: 0044-8249
Publication type: Academic Journal
DOI: 10.1002/ange.201609111

Regioselective One-Pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates.

Umezu, Satoshi; dos Passos Gomes, Gabriel; Yoshinaga, Tatsuro; Sakae, Mikei; Matsumoto, Kenji; Iwata, Takayuki; Alabugin, Igor; Shindo, Mitsuru