Construction of Condensed Polycyclic Aromatic Frameworks through Intramolecular Cycloaddition Reactions Involving Arynes Bearing an Internal Alkyne Moiety

Suguru Yoshida, Keita Shimizu, Keisuke Uchida, Yuki Hazama, Kazunobu Igawa, Katsuhiko Tomooka, Takamitsu Hosoya

研究成果: Contribution to journalArticle査読

21 被引用数 (Scopus)

抄録

Facile synthetic methods for condensed polycyclic aromatic compounds via aryne intermediates are reported. The generation of arynes bearing a (3-arylpropargyl)oxy group from the corresponding o-iodoaryl triflate-type precursors efficiently afforded arene-fused oxaacenaphthene derivatives, which were formed through intramolecular [2+4] cycloaddition. Extending the method to the generation of arynes bearing a 1,3-diyne moiety led to a continuous generation of naphthalyne intermediate through the hexadehydro Diels–Alder reaction involving the aryne triple bond. This novel type of aryne-relay chemistry enabled the synthesis of a unique aminoarylated oxaacenaphthene derivative and highly ring-fused anthracene derivatives.

本文言語英語
ページ(範囲)15332-15335
ページ数4
ジャーナルChemistry - A European Journal
23
61
DOI
出版ステータス出版済み - 11 2 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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