Synthesis of Furo[2,3-f]dibenzotropones via Intramolecular Wittig Reaction of Alkylidene Dibenzo-β-tropolones

Po Chung Chien; Yi Ru Chen; You Jie Chen; Ching Fen Chang; Gangababu Marri; Wenwei Lin

doi:10.1002/adsc.202301344

Synthesis of Furo[2,3-f]dibenzotropones via Intramolecular Wittig Reaction of Alkylidene Dibenzo-β-tropolones

Po Chung Chien, Yi Ru Chen, You Jie Chen, Ching Fen Chang, Gangababu Marri, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

A strategy was developed for synthesizing furan-fused dibenzotropones via intramolecular Wittig reactions of alkylidene dibenzo-β-tropolones and acylating reactants in catalytic or stoichiometric conditions. With these protocols, a series of furo[2,3-f]dibenzotropones were obtained in 49–99% yields within 1–10 hours. Mechanistic studies of the base-free phenomena revealed that the organophosphane acts both as a mediator and a regenerable Brønsted base under heating.

Original language	English
Pages (from-to)	420-425
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	366
Issue number	3
DOIs	https://doi.org/10.1002/adsc.202301344
Publication status	Published - 2024 Feb 19

Keywords

Fused-ring systems
Organocatalysis
Oxygen heterocycles
Tropone
Wittig reactions

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.202301344

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title = "Synthesis of Furo[2,3-f]dibenzotropones via Intramolecular Wittig Reaction of Alkylidene Dibenzo-β-tropolones",

abstract = "A strategy was developed for synthesizing furan-fused dibenzotropones via intramolecular Wittig reactions of alkylidene dibenzo-β-tropolones and acylating reactants in catalytic or stoichiometric conditions. With these protocols, a series of furo[2,3-f]dibenzotropones were obtained in 49–99% yields within 1–10 hours. Mechanistic studies of the base-free phenomena revealed that the organophosphane acts both as a mediator and a regenerable Br{\o}nsted base under heating.",

keywords = "Fused-ring systems, Organocatalysis, Oxygen heterocycles, Tropone, Wittig reactions",

author = "Chien, {Po Chung} and Chen, {Yi Ru} and Chen, {You Jie} and Chang, {Ching Fen} and Gangababu Marri and Wenwei Lin",

note = "Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

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doi = "10.1002/adsc.202301344",

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T1 - Synthesis of Furo[2,3-f]dibenzotropones via Intramolecular Wittig Reaction of Alkylidene Dibenzo-β-tropolones

AU - Chien, Po Chung

AU - Chen, Yi Ru

AU - Chen, You Jie

AU - Chang, Ching Fen

AU - Marri, Gangababu

AU - Lin, Wenwei

PY - 2024/2/19

Y1 - 2024/2/19

N2 - A strategy was developed for synthesizing furan-fused dibenzotropones via intramolecular Wittig reactions of alkylidene dibenzo-β-tropolones and acylating reactants in catalytic or stoichiometric conditions. With these protocols, a series of furo[2,3-f]dibenzotropones were obtained in 49–99% yields within 1–10 hours. Mechanistic studies of the base-free phenomena revealed that the organophosphane acts both as a mediator and a regenerable Brønsted base under heating.

AB - A strategy was developed for synthesizing furan-fused dibenzotropones via intramolecular Wittig reactions of alkylidene dibenzo-β-tropolones and acylating reactants in catalytic or stoichiometric conditions. With these protocols, a series of furo[2,3-f]dibenzotropones were obtained in 49–99% yields within 1–10 hours. Mechanistic studies of the base-free phenomena revealed that the organophosphane acts both as a mediator and a regenerable Brønsted base under heating.

KW - Fused-ring systems

KW - Organocatalysis

KW - Oxygen heterocycles

KW - Tropone

KW - Wittig reactions

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Synthesis of Furo[2,3-f]dibenzotropones via Intramolecular Wittig Reaction of Alkylidene Dibenzo-β-tropolones

Abstract

Keywords

ASJC Scopus subject areas

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