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

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

Alexandre Rossignon, Davide BONIFAZI

Universite de Namur

Résultats de recherche: Contribution à un journal/une revue › Article de revue › Revue par des pairs

Résumé

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.

langue originale	Anglais
Pages (de - à)	3588-3599
Nombre de pages	12
journal	Synthesis
Volume	51
Numéro de publication	19
Les DOIs	https://doi.org/10.1055/s-0037-1611892
Etat de la publication	Publié - 1 janv. 2019

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10.1055/s-0037-1611892

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Synthesis, optoelectronic properties and hydrogen-bond promoted organisation of heteroatom-doped polycyclic hydrocarbons
ROSSIGNON, A. (Auteur), VINCENT, S. (Promoteur), BONIFAZI, D. (Promoteur), APRILE, C. (Jury), VINCENT, S. (Jury), Gerbaux, P. (Jury) & Kivala, M. (Jury), 6 juil. 2020
Student thesis: Doc types › Docteur en Sciences

Contient cette citation

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

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.",

keywords = "C-H activation, C-O bond formation, cularine, cyclic diaryl ether, cycloetherification, furans, O-annulation, oxidative cyclisation, pyrans",

author = "Alexandre Rossignon and Davide BONIFAZI",

note = "Funding Information: D. B. thanks the EU through the MC-RISE scheme (INFUSION), and the School of Chemistry @Cardiff University for the financial support.() Publisher Copyright: {\textcopyright} 2019 Thieme. All rights reserved.",

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doi = "10.1055/s-0037-1611892",

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AU - Rossignon, Alexandre

AU - BONIFAZI, Davide

N1 - Funding Information: D. B. thanks the EU through the MC-RISE scheme (INFUSION), and the School of Chemistry @Cardiff University for the financial support.() Publisher Copyright: © 2019 Thieme. All rights reserved.

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N2 - 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.

AB - 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.

KW - C-H activation

KW - C-O bond formation

KW - cularine

KW - cyclic diaryl ether

KW - cycloetherification

KW - furans

KW - O-annulation

KW - oxidative cyclisation

KW - pyrans

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ER -

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

Résumé

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Thèses de l'étudiant

Synthesis, optoelectronic properties and hydrogen-bond promoted organisation of heteroatom-doped polycyclic hydrocarbons

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