4.6 Article

Anthranoxides as Highly Reactive Arynophiles for the Synthesis of Triptycenes

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 26, 期 39, 页码 8506-8510

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202002065

关键词

anthracene; benzyne; cycloaddition; DFT; triptycene

资金

  1. JSPS KAKENHI [JP18H02557, JP18H04418, JP18H04624, JP17K14449, JP20H04780, JP20K15283]
  2. Asahi Glass Foundation
  3. Qdai-jump Research Program Wakaba Challenge at Kyushu University
  4. IRCCS Fusion Emergent Research Program

向作者/读者索取更多资源

We report herein an efficient method to synthesize triptycenes by the reaction of benzynes and anthranoxides, which are electron-rich and readily prepared from the corresponding anthrones. Using this method, 1,9-syn-substituted triptycenes were regioselectively obtained employing 3-methoxybenzynes. This method was also applied to synthesize pentiptycenes. A DFT study revealed that the cycloaddition of lithium anthranoxide and benzyne proceeds stepwise.

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