Oxidation of Phenols

Yamamura, Shosuke

doi:10.1002/9780470682531.pat0293

Cited by 4 publications

(2 citation statements)

References 347 publications

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“…9g,10 This is because, upon the initial single-electron oxidation, phenols are converted into phenoxyl radicals, which are prone to dimerization and other side processes (Scheme 3a ). 7a , 7` d e These undesired pathways mitigate the efficiency of the spirooxacyclization by competing with the second oxidation step that is required to generate a phenoxenium ion, priming the ring for the addition of the oxygen nucleophile. Conversely, the SET oxidation of aryl methyl ethers affords the corresponding radical cations (Scheme 3b ), which are readily quenched by the nucleophile, preventing the formation of side products.…”

Section: Table 1 Effect Of Reaction Parameters On the E...mentioning

confidence: 99%

Electrochemical Dearomatizing Spirolactonization and Spiroetherification of Naphthols and Phenols

2023

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An electrochemical oxidative ortho-dearomatization of naphthols and phenols with an intramolecular C–O bond formation has been developed. A careful optimization of the reaction parameters allowed for the application of free phenols as the starting materials, in contrast to the existing alternative procedures necessitating aryl methyl ethers substrates. The reaction delivers an array of spirolactones and spiroethers in yields up to 97%, under simple experimental conditions: in a constant current mode, using an undivided cell, and without an inert atmosphere. The method avoids using catalysts or stoichiometric oxidants (e.g., hypervalent iodine reagents), generating hydrogen as the sole by-product.

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Section: Table 1 Effect Of Reaction Parameters On the E...mentioning

confidence: 99%

Electrochemical Dearomatizing Spirolactonization and Spiroetherification of Naphthols and Phenols

2023

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“…Electrochemical oxidation of phenols yields new complex architectures resulting from C-C and/or C-O bond formation. 1 Such radical coupling products represent highly versatile intermediates in the synthesis of more sophisticated structures. However, some of them are building blocks in biosynthetical pathways or show biological activity.…”

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confidence: 99%