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

University of Namur

Research output: Contribution to journal › Review article › peer-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 language	English
Pages (from-to)	3588-3599
Number of pages	12
Journal	Synthesis
Volume	51
Issue number	19
DOIs	https://doi.org/10.1055/s-0037-1611892
Publication status	Published - 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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10.1055/s-0037-1611892

Cite this

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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.",

year = "2019",

month = jan,

day = "1",

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

language = "English",

volume = "51",

pages = "3588--3599",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

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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.

PY - 2019/1/1

Y1 - 2019/1/1

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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U2 - 10.1055/s-0037-1611892

DO - 10.1055/s-0037-1611892

M3 - Review article

AN - SCOPUS:85072334207

SN - 0039-7881

VL - 51

SP - 3588

EP - 3599

JO - Synthesis

JF - Synthesis

IS - 19

ER -

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

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

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

Abstract

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Keywords

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Student theses

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

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