A scalable and green one-minute synthesis of substituted phenols

A mild, green and highly efficient protocol was developed for the synthesis of substituted phenols via ipso -hydroxylation of arylboronic acids in ethanol. The method utilizes the combination of aqueous hydrogen peroxide as the oxidant and H 2 O 2 /HBr as the reagent under unprecedentedly simple and...

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Bibliographic Details
Published in:RSC advances 2020-11, Vol.1 (66), p.4582-4587
Main Authors: Elumalai, Vijayaragavan, Hansen, Jørn H
Format: Article
Language:English
Subjects:
Bromination
Chemistry
Chemistry: 440
Cross coupling
Ethanol
Hydrogen peroxide
Hydroxylation
Kjemi: 440
Matematikk og Naturvitenskap: 400
Mathematics and natural science: 400
Oxidizing agents
Phenols
Reaction time
Reagents
Room temperature
Substitutes
Synthesis
VDP
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Summary:A mild, green and highly efficient protocol was developed for the synthesis of substituted phenols via ipso -hydroxylation of arylboronic acids in ethanol. The method utilizes the combination of aqueous hydrogen peroxide as the oxidant and H 2 O 2 /HBr as the reagent under unprecedentedly simple and convenient conditions. A wide range of arylboronic acids were smoothly transformed into substituted phenols in very good to excellent yields without chromatographic purification. The reaction is scalable up to at least 5 grams at room temperature with one-minute reaction time and can be combined in a one-pot sequence with bromination and Pd-catalyzed cross-coupling to generate more diverse, highly substituted phenols. The synthesis of highly substituted phenols is advanced via a green one minute hydroxylation and subsequent one-pot functionalizations.
ISSN:2046-2069
2046-2069
DOI:10.1039/d0ra08580d