Synthesis of renewable isoindolines from bio-based furfurals

Upgrading biomass-derived platforms to functionalized aromatics by a tandem Diels-Alder (DA) cycloaddition-aromatization strategy has attracted broad attention. However, three challenges exist: improving the equilibrium of DA cycloaddition, controlling the regioselectivity of DA adducts, and increas...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 25; no. 8; pp. 3297 - 335
Main Authors Xu, Feng, Li, Zao, Zhang, Li-Long, Liu, Shengqi, Li, Hu, Liao, Yuhe, Yang, Song
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 24.04.2023
Royal Society of Chemistry
Subjects
Adducts
Aromatic compounds
Catalysts
Chemistry
Chemistry, Multidisciplinary
Cycloaddition
Diels-Alder reactions
Green & Sustainable Science & Technology
Green chemistry
Ionic liquids
Liquid phases
Physical Sciences
Regioselectivity
Science & Technology
Science & Technology - Other Topics
Thermal stability
BIOMASS-DERIVED FURAN
2,5-DIMETHYLFURAN
ETHYLENE
P-XYLENE
CONVERSION
CATALYZED REDUCTIVE ALKOXYLATION
ONE-POT
ACRYLIC-ACID
EFFICIENT
DIELS-ALDER CYCLOADDITION
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Abstract Upgrading biomass-derived platforms to functionalized aromatics by a tandem Diels-Alder (DA) cycloaddition-aromatization strategy has attracted broad attention. However, three challenges exist: improving the equilibrium of DA cycloaddition, controlling the regioselectivity of DA adducts, and increasing the stability of the cycloadduct. Herein, an intramolecular cycloaromatization strategy was developed for the direct upgradation of bio-furfurals to isoindolinones under liquid phase conditions via the selective formation of exo -DA adducts. The efficiency of the intramolecular DA cycloaddition was remarkably promoted by a defective Zn-BTC-SA catalyst quantitatively forming the desired regioselective exo -DA cycloadduct with higher thermal stability. Meanwhile, the co-existence of an acidic ionic liquid ([Hmim]HSO 4 ) could facilitate the subsequent aromatization to generate isoindolinones in quantitative yields. Theoretical calculations elaborated the significance of the in situ formed exo -DA adducts with enhanced stability in the cascade conversion process. Moreover, this protocol is applicable to the production of a wide range of renewable isoindolinone derivatives and commercial medicines in excellent yields (>92%) and is suitable for gram-scale reactions. Sugar aromatization: the efficient conversion of bio-furanics to versatile renewable isoindolinones is achieved by a self-stabilized cycloaromatization strategy.
AbstractList Upgrading biomass-derived platforms to functionalized aromatics by a tandem Diels-Alder (DA) cycloaddition-aromatization strategy has attracted broad attention. However, three challenges exist: improving the equilibrium of DA cycloaddition, controlling the regioselectivity of DA adducts, and increasing the stability of the cycloadduct. Herein, an intramolecular cycloaromatization strategy was developed for the direct upgradation of bio-furfurals to isoindolinones under liquid phase conditions via the selective formation of exo -DA adducts. The efficiency of the intramolecular DA cycloaddition was remarkably promoted by a defective Zn-BTC-SA catalyst quantitatively forming the desired regioselective exo -DA cycloadduct with higher thermal stability. Meanwhile, the co-existence of an acidic ionic liquid ([Hmim]HSO 4 ) could facilitate the subsequent aromatization to generate isoindolinones in quantitative yields. Theoretical calculations elaborated the significance of the in situ formed exo -DA adducts with enhanced stability in the cascade conversion process. Moreover, this protocol is applicable to the production of a wide range of renewable isoindolinone derivatives and commercial medicines in excellent yields (>92%) and is suitable for gram-scale reactions. Sugar aromatization: the efficient conversion of bio-furanics to versatile renewable isoindolinones is achieved by a self-stabilized cycloaromatization strategy.
Upgrading biomass-derived platforms to functionalized aromatics by a tandem Diels–Alder (DA) cycloaddition–aromatization strategy has attracted broad attention. However, three challenges exist: improving the equilibrium of DA cycloaddition, controlling the regioselectivity of DA adducts, and increasing the stability of the cycloadduct. Herein, an intramolecular cycloaromatization strategy was developed for the direct upgradation of bio-furfurals to isoindolinones under liquid phase conditions via the selective formation of exo-DA adducts. The efficiency of the intramolecular DA cycloaddition was remarkably promoted by a defective Zn-BTC-SA catalyst quantitatively forming the desired regioselective exo-DA cycloadduct with higher thermal stability. Meanwhile, the co-existence of an acidic ionic liquid ([Hmim]HSO4) could facilitate the subsequent aromatization to generate isoindolinones in quantitative yields. Theoretical calculations elaborated the significance of the in situ formed exo-DA adducts with enhanced stability in the cascade conversion process. Moreover, this protocol is applicable to the production of a wide range of renewable isoindolinone derivatives and commercial medicines in excellent yields (>92%) and is suitable for gram-scale reactions.
Upgrading biomass-derived platforms to functionalized aromatics by a tandem Diels–Alder (DA) cycloaddition–aromatization strategy has attracted broad attention. However, three challenges exist: improving the equilibrium of DA cycloaddition, controlling the regioselectivity of DA adducts, and increasing the stability of the cycloadduct. Herein, an intramolecular cycloaromatization strategy was developed for the direct upgradation of bio-furfurals to isoindolinones under liquid phase conditions via the selective formation of exo -DA adducts. The efficiency of the intramolecular DA cycloaddition was remarkably promoted by a defective Zn-BTC-SA catalyst quantitatively forming the desired regioselective exo -DA cycloadduct with higher thermal stability. Meanwhile, the co-existence of an acidic ionic liquid ([Hmim]HSO 4 ) could facilitate the subsequent aromatization to generate isoindolinones in quantitative yields. Theoretical calculations elaborated the significance of the in situ formed exo -DA adducts with enhanced stability in the cascade conversion process. Moreover, this protocol is applicable to the production of a wide range of renewable isoindolinone derivatives and commercial medicines in excellent yields (>92%) and is suitable for gram-scale reactions.
Author Li, Hu
Xu, Feng
Yang, Song
Li, Zao
Liu, Shengqi
Zhang, Li-Long
Liao, Yuhe
AuthorAffiliation State-Local Joint Laboratory for Comprehensive Utilization of Biomass
Guiyang University
Ministry of Education
Chinese Academy of Sciences
Center for R&D of Fine Chemicals
Key Laboratory of Green Pesticide & Agricultural Bioengineering
Guizhou University
National Key Laboratory of Green Pesticide
Department of Chemistry and Materials Engineering
Guangzhou Institute of Energy Conversion
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Issue 8
Keywords BIOMASS-DERIVED FURAN
2,5-DIMETHYLFURAN
ETHYLENE
P-XYLENE
CONVERSION
CATALYZED REDUCTIVE ALKOXYLATION
ONE-POT
ACRYLIC-ACID
EFFICIENT
DIELS-ALDER CYCLOADDITION
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Snippet Upgrading biomass-derived platforms to functionalized aromatics by a tandem Diels-Alder (DA) cycloaddition-aromatization strategy has attracted broad...
Upgrading biomass-derived platforms to functionalized aromatics by a tandem Diels–Alder (DA) cycloaddition–aromatization strategy has attracted broad...
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SubjectTerms Adducts
Aromatic compounds
Catalysts
Chemistry
Chemistry, Multidisciplinary
Cycloaddition
Diels-Alder reactions
Green & Sustainable Science & Technology
Green chemistry
Ionic liquids
Liquid phases
Physical Sciences
Regioselectivity
Science & Technology
Science & Technology - Other Topics
Thermal stability
Title Synthesis of renewable isoindolines from bio-based furfurals
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