O-Annulation Leading to Five-, Six-, and Seven-Membered Cyclic Diaryl Ethers Involving C-H Cleavage

Research output: Contribution to journalReview articlepeer-review

Abstract

Cyclic diaryl ethers are present in multiple natural compounds, organic pollutants as well as in π-conjugated organic molecular materials. This short review aims at overviewing the main synthetic advances in the O-annulation methods for preparing five-, six-, and seven-membered rings through C-H cleavage. 1 Introduction 2 Five-Membered Rings: The Dibenzofuran (DBF) Motif 2.1 Palladium-Catalysed C-H Activation 2.2 Copper-Catalysed C-H Activation 2.3 Non-CH Activation Oxidant-Mediated Cyclisation 2.4 Light-Mediated Cyclisation 2.5 Acid-catalysed C-O Cleavage/C-O Formation 3 Six-Membered Rings: DBX, PXX, Xanthone, and Their Derivatives 3.1 Dibenzoxanthene (DBX) 3.2 Peri -Xanthenoxanthene (PXX) 3.3 Xanthones 3.4 Miscellaneous 4 Seven-Membered Rings: Cularine 5 Conclusion.

Original languageEnglish
Pages (from-to)3588-3599
Number of pages12
JournalSynthesis
Volume51
Issue number19
DOIs
Publication statusPublished - 1 Jan 2019

Funding

D. B. thanks the EU through the MC-RISE scheme (INFUSION), and the School of Chemistry @Cardiff University for the financial support.() A. R. thanks the FRS-FNRS for his FRIA fellowship. D.B. thanks all present and past co-workers Dr. D. Stassen, Dr. A. Berezin, Dr. A. Sciutto, Dr. D. Biloborodov, Dr. L. Dordevich, Dr. D. Milano, Mr. C. Valentini, and Mr. A. Rossignon for their dedication and achievements in the field of C–O bond formation.

Keywords

  • C-H activation
  • C-O bond formation
  • cularine
  • cyclic diaryl ether
  • cycloetherification
  • furans
  • O-annulation
  • oxidative cyclisation
  • pyrans

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