Palladium‐Assisted “Aromatic Metamorphosis” of Dibenzothiophenes into Triphenylenes

DOI DOI DOI 機関リポジトリ (HANDLE) HANDLE ほか5件をすべて表示 一部だけ表示 研究データあり 被引用文献31件 参考文献112件 オープンアクセス

書誌事項

タイトル別名
  • Palladium-assisted "aromatic metamorphosis" of dibenzothiophenes into triphenylenes.
公開日
2015-05-04
資源種別
journal article
権利情報
  • This is the peer reviewed version of the following article: Vasu, D., Yorimitsu, H. and Osuka, A. (2015), Palladium-Assisted "Aromatic Metamorphosis" of Dibenzothiophenes into Triphenylenes. Angew. Chem. Int. Ed., 54: 7162–7166, which has been published in final form at http://dx.doi.org/10.1002/anie.201501992. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
  • The full-text file will be made open to the public on 4 May 2016 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
  • This is not the published version. Please cite only the published version.
  • この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
DOI
  • 10.1002/anie.201501992
  • 10.1002/ange.201501992
  • 10.1002/chin.201542130
公開者
wiley

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説明

Two new palladium-catalyzed reactions of aromatic sulfur compounds enabled the conversion of dibenzothiophenes into triphenylenes in four steps. This transformation of one aromatic framework into another consists of 1) 4-chlorobutylation of the dibenzothiophene to form the corresponding sulfonium salt, 2) palladium-catalyzed arylative ring opening of the sulfonium salt with a sodium tetraarylborate, 3) an intramolecular S(N)2 reaction to form a teraryl sulfonium salt, and 4) palladium-catalyzed intramolecular C-S/C-H coupling through electrophilic palladation. Symmetrical as well as unsymmetrical triphenylenes of interest were synthesized in a tailor-made fashion in satisfactory overall yields.

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