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

@article{Umezu2017RegioselectiveOS,
  title={Regioselective One-Pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates.},
  author={Satoshi Umezu and Gabriel Dos Passos Gomes and Tatsuro Yoshinaga and Mikei Sakae and Kenji Matsumoto and Takayuki Iwata and Igor V. Alabugin and Mitsuru Shindo},
  journal={Angewandte Chemie},
  year={2017},
  volume={56 5},
  pages={1298-1302}
}
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… CONTINUE READING