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 (Germany)
Volume	51
Issue number	19
DOIs	https://doi.org/10.1055/s-0037-1611892
Publication status	Published - 1 Jan 2019

Keywords

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

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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",

year = "2019",

month = jan,

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

language = "English",

volume = "51",

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AU - Rossignon, Alexandre

AU - BONIFAZI, Davide

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

VL - 51

SP - 3588

EP - 3599

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 19

ER -

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

Abstract

Keywords

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