Bare Magnetite-Promoted Oxidative Hydroxylation of Arylboronic Acids and Subsequent Conversion into Phenolic Compounds

Abstract

The simple combination of readily available, recoverable, and recyclable magnetite (Fe₃O₄) nanoparticles and an environmentally friendly oxidant (H₂O₂) induced the effective functional group transformation of arylboronic acids into their corresponding phenols under mild conditions. Moreover, subsequent treatment of the reaction intermediate with appropriate electrophiles was accomplished in a one-pot system, leading to the formation of halophenols and phenolic derivatives.

Key words

magnetite - H₂O₂ - ipso-hydroxylation - arylboronic acids - phenols

Publikationsverlauf

Eingereicht: 29. März 2022

Angenommen nach Revision: 06. Mai 2022

Artikel online veröffentlicht:
03. Juni 2022

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• 32 A representative procedure for the ipso-hydroxylation: A flask containing a Fe₃O₄@magnetic bar was charged with phenylboronic acid (3.0 mmol), and H₂O₂ (aq. 30 wt%, 0.3 mL). Then, the mixture was stirred at room temperature in open air for 5 min. The resulting mixture was then extracted with ethyl acetate (3 × 10 mL). The combined organic layers were washed with water, then dried with anhydrous Na₂SO₄, and evaporated under reduced pressure. The crude mixture was purified by column chromatography on silica gel (hexanes/ethyl acetate) to give phenol (2a) in 99% isolate yield as a colorless oily liquid. ¹H NMR (400 MHz, CDCl₃): δ = 7.28 (t, J = 8.4 Hz, 2 H), 6.99–6.95 (m, 1 H), 6.89–6.85 (m, 2 H), 4.80 (br s, 1 H) ppm. ¹³C NMR (100 MHz, CDCl₃): δ = 155.4, 129.7, 120.9, 115.3 ppm.