Protection for Phenols and Catechols

Wuts, Peter G. M.; Greene, Theodora W.

doi:10.1002/9780470053485.ch3

Cited by 14 publications

(1 citation statement)

References 380 publications

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“…This allows them to be used in orthogonal protecting group strategies and many procedures have been established for their removal. [1][2][3][4][5] Whilst these methods give the corresponding alcohols in high yields and show good functional group tolerance, the vast majority employ catalysts based on palladium and rhodium. Due to ever increasing cost and diminishing availability, there is considerable current interest in efforts to substitute processes mediated by palladium group metals (such as cross couplings) with more readily available transition metals.…”

Section: Introductionmentioning

confidence: 99%

A mild copper catalyzed method for the selective deprotection of aryl allyl ethers

Hemming

Talbot

Steel

2017

Tetrahedron Letters

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Section: Introductionmentioning

confidence: 99%

A mild copper catalyzed method for the selective deprotection of aryl allyl ethers

Hemming

Talbot

Steel

2017

Tetrahedron Letters

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Quantum Dot‐Catalyzed Photoreductive Removal of Sulfonyl‐Based Protecting Groups

2020

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This Communication describes the use of CuInS 2 / ZnS quantum dots (QDs) as photocatalysts for the reductive deprotection of aryl sulfonyl-protected phenols. For a series of aryl sulfonates with electron-withdrawing substituents, the rate of deprotection for the corresponding phenyl aryl sulfonates increases with decreasing electrochemical potential for the two electron transfers within the catalytic cycle. The rate of deprotection for a substrate that contains a carboxylic acid, a known QD-binding group, is accelerated by more than a factor of ten from that expected from the electrochemical potential for the transformation, a result that suggests that formation of metastable electron donor-acceptor complexes provides a significant kinetic advantage. This deprotection method does not perturb the common NHBoc or toluenesulfonyl protecting groups and, as demonstrated with an estrone substrate, does not perturb proximate ketones, which are generally vulnerable to many chemical reduction methods used for this class of reactions.

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Advancements and Perspectives toward Lignin Valorization via O‐Demethylation

Wu,

Smet,

Brandi

et al. 2024

Angewandte Chemie

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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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Protection for Phenols and Catechols

Cited by 14 publications

References 380 publications

A mild copper catalyzed method for the selective deprotection of aryl allyl ethers

A mild copper catalyzed method for the selective deprotection of aryl allyl ethers

Quantum Dot‐Catalyzed Photoreductive Removal of Sulfonyl‐Based Protecting Groups

Advancements and Perspectives toward Lignin Valorization via O‐Demethylation

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