Synthesis of 9,10-Diarylanthracenes via Mg(TMP) 2 ·2LiCl-Mediated Benzyne Generation/[4+2] Cycloaddition and Deoxygenation of 9,10-Epoxyanthracene Intermediates

Naoya Miyamoto, Yuki Nakazawa, Takanori Nakamura, Kentaro Okano, Sota Sato, Zhe Sun, Hiroyuki Isobe, Hidetoshi Tokuyama

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A new synthetic route to functionalized 9,10-diarylanthracenes has been developed. 9,10-Epoxyanthracene intermediates were prepared by [4+2] cycloaddition of 1,3-diarylisobenzofuran with a variety of functionalized benzyne intermediates, which were obtained by Mg(TMP) 2 ·2LiCl-mediated benzyne generation. For the cleavage of the resultant 9,10-epoxyanthracene intermediates, we developed mild deoxygenation conditions using a combination of trifluoroacetic acid and Et 3 SiH. The utility of this sequence was demonstrated by application to the synthesis of 5,7,12,14-tetraphenylpentacene.

Original languageEnglish
Article numberst-2017-u0659-l
Pages (from-to)513-518
Number of pages6
JournalSynlett
Volume29
Issue number4
DOIs
Publication statusPublished - 2018 Mar 1

Keywords

  • anthracene
  • arynes
  • cycloaddition
  • deoxygenation
  • furanes
  • pentacene

ASJC Scopus subject areas

  • Organic Chemistry

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