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

Alexandre Rossignon; Davide Bonifazi

doi:10.1055/s-0037-1611892

Synthesis, Table of Contents

Synthesis 2019; 51(19): 3588-3599
DOI: 10.1055/s-0037-1611892

short review

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

Authors

Alexandre Rossignon

^aDepartment of Chemistry, University of Namur, Rue de Bruxelles 61, Namur 5000, Belgium

^bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, Wales, UK Email: bonifazid@cardiff.ac.uk
Davide Bonifazi ∗

^bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, Wales, UK Email: bonifazid@cardiff.ac.uk

Abstract

All articles of this category

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

Key words

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

Full Text

References

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