Tautomeric Equilibria and Rearrangements Involving Phenols

Koblik, A. V.

doi:10.1002/9780470682531.pat0287

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■ Introduction1

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2024

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“…3 Phenols have been a concern all the time because they are not only widely applied in various chemistry but also indispensable as antioxidants in cosmetics, health products, and so on. 4 From an atom-and step-economic perspective, the direct catalytic dehydrative substitution of alcohols with phenols is an ideal method to functionalize phenols. 5 However, reports in this respect are quite limited.…”

Section: ■ Introductionmentioning

confidence: 99%

Dehydrative Alkylation of Phenols with Alcohols via Formation of Triflate

Ni,

Zhou,

Zhang

et al. 2024

J. Org. Chem.

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An efficient synergistic trityl cation ([Ph 3 C][B(C 6 F 5 ) 4 ])/triflic anhydride (Tf 2 O) catalyzed alkylation of phenols with alcohols is reported. Benefiting from the formation of the triflate in situ, cheap and readily available active alcohols can be used as the alkylating reagents, and the reaction proceeds under mild reaction conditions with a broad substrate scope. This protocol enables the synthesis of ortho-selective phenols and 2,4,6-trisubstitued phenols containing three different alkyl groups. tert-Amyl triflate was synthesized, and mechanistic studies support a triflate-mediated alkylation process.

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Section: ■ Introductionmentioning

confidence: 99%