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