Utilization of catecholic functionality in natural safrole and eugenol to synthesize mussel-inspired polymers

Alhaffar, Mouheddin T.; Akhtar, M. Naseem; Ali, Shaikh A.

doi:10.1039/c9ra04719k

“…Otherwise, phenolic group may react with m-CPBA generating byproducts. The protection can be achieved with acetic anhydride (Ac 2 O) 89 or with silyl groups 90 among other phenolic protecting groups. Note that silanes also react with the methoxide group of eugenol and thus the subsequent deprotection leads to a catechol group as detailed in Section 3.4.2.…”

Section: Epoxidationmentioning

confidence: 99%

“…However, this kind of protection can be useful since other protecting groups may be cleaved or react during successive chemical transformations. 90 Epoxidation on the allylic double bond could also be done using Oxone® (potassium peroxymonosulfate) and a mixture of water and acetone as solvents. 91 The use of Oxone® instead of m-CPBA is a greener alternative since Oxone® is not a chlorinated oxidizing agent and atom economy is improved.…”

Section: Epoxidationmentioning

confidence: 99%

“…Note that silanes also react with the methoxide group of eugenol and thus the subsequent deprotection leads to a catechol group as detailed in section . However, this kind of protection can be useful, since other protecting groups may be cleaved or react during successive chemical transformations . Epoxidation on the allylic double bond could also be done using Oxone (potassium peroxymonosulfate) and a mixture of water and acetone as solvents .…”

Section: Eugenol: Reactivity and Functionalizationmentioning

confidence: 99%

“…The methoxy group of eugenol, as well as the hydroxyl phenolic group, can react with silanes. 90 The reaction can be carried out with diphenylsilane, a silyl protecting group, in the presence of tris-(pentafluorophenyl)borane as displayed in Scheme 12b. The silane reacts with both the methoxy and the phenolic hydroxyl group.…”

Section: Eugenol: Reactivity and Functionalizationmentioning

confidence: 99%

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Lignin represents the largest aromatic carbon resource in plants, holding significant promise as a renewable feedstock for bioaromatics and other cyclic hydrocarbons in the context of the circular bioeconomy. However, the methoxy groups of aryl methyl ethers, abundantly found in technical lignins and lignin‐derived chemicals, limit their pertinent chemical reactivity and broader applicability. Unlocking the phenolic hydroxyl functionality through O‐demethylation (ODM) has emerged as a valuable approach to mitigate this need and enables further applications. In this review, we provide a comprehensive summary of the progress in the valorization of technical lignin and lignin‐derived chemicals via ODM, both catalytic and non‐catalytic reactions. Furthermore, a detailed analysis of the properties and potential applications of the O‐demethylated products is presented, accompanied by a systematic overview of available ODM reactions. This review primarily focuses on enhancing the phenolic hydroxyl content in lignin‐derived species through ODM, showcasing its potential in the catalytic funneling of lignin and value‐added applications. A comprehensive synopsis and future outlook are included in the concluding section of this review.

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View full text Add to dashboard Cite

Lignin represents the largest aromatic carbon resource in plants, holding significant promise as a renewable feedstock for bioaromatics and other cyclic hydrocarbons in the context of the circular bioeconomy. However, the methoxy groups of aryl methyl ethers, abundantly found in technical lignins and lignin‐derived chemicals, limit their pertinent chemical reactivity and broader applicability. Unlocking the phenolic hydroxyl functionality through O‐demethylation (ODM) has emerged as a valuable approach to mitigate this need and enables further applications. In this review, we provide a comprehensive summary of the progress in the valorization of technical lignin and lignin‐derived chemicals via ODM, both catalytic and non‐catalytic reactions. Furthermore, a detailed analysis of the properties and potential applications of the O‐demethylated products is presented, accompanied by a systematic overview of available ODM reactions. This review primarily focuses on enhancing the phenolic hydroxyl content in lignin‐derived species through ODM, showcasing its potential in the catalytic funneling of lignin and value‐added applications. A comprehensive synopsis and future outlook are included in the concluding section of this review.

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Utilization of catecholic functionality in natural safrole and eugenol to synthesize mussel-inspired polymers

Abstract: Naturally occurring safrole I upon epoxidation gave safrole oxide II, which underwent polymerization using a Lewis acid initiator/catalyst of triphenylmethylphosphonium bromide/triisobutylaluminum to afford new polyether III in excellent yields.

Cited by 9 publications

References 54 publications

Eugenol, a Promising Building Block for Biobased Polymers with Cutting-Edge Properties

Eugenol, a Promising Building Block for Biobased Polymers with Cutting-Edge Properties

Advancements and Perspectives toward Lignin Valorization via O‐Demethylation

Advancements and Perspectives toward Lignin Valorization via O‐Demethylation

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