Green Photoorganocatalytic Synthesis of Phenols from Arylboronic Acids

Ioanna K. Sideri; Errika Voutyritsa; Christoforos G. Kokotos

doi:10.1055/s-0036-1591837

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(10): 1324-1328
DOI: 10.1055/s-0036-1591837

letter

Green Photoorganocatalytic Synthesis of Phenols from Arylboronic Acids

Ioanna K. Sideri

Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, Athens 15771, Greece eMail: ckokotos@chem.uoa.gr

,

Errika Voutyritsa

Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, Athens 15771, Greece eMail: ckokotos@chem.uoa.gr

,

Christoforos G. Kokotos*

Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, Athens 15771, Greece eMail: ckokotos@chem.uoa.gr

› Institutsangaben

Abstract

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Published as part of the Special Section 9^th EuCheMS Organic Division Young Investigator Workshop

Abstract

A green and cheap protocol for the photocatalytic hydroxylation of arylboronic acids is presented. 2,2-Dimethoxy-2-phenylacetophenone proved to be the best photoinitiator, among a range of organocatalysts in promoting this reaction. This photocatalytic protocol can be expanded into a wide substrate scope of aromatic boronic acids bearing various functional groups, leading to the corresponding phenols in good to high yields under mild reaction conditions, which include water as solvent, light irradiation provided from standard light-bulbs at room temperature.

Key words

photoorganocatalysis - hydroxylation - arylboronic acid - phenols - green chemistry

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Referenzen

References and Notes

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26 General Procedure for the Photoorganocatalytic Hydroxylation of Arylboronic Acids The boronic acid (0.60 mmol) was placed in a glass vial and dissolved in water (1.0 mL), followed by 2,2-dimethoxy-2-phenylacetophenone (30.0 mg, 0.12 mmol). DIPEA (580 mg, 4.50 mmol) was then added. The reaction mixture was left open to the atmosphere with stirring at room temperature under standard light-bulb irradiation (2 × 80 W household lamps) for 72 h. The reaction mixture was quenched with HCl (1 M, 20 mL) and then extracted with Et₂O (20 mL). The organic layer was washed with brine (20 mL) and dried over Na₂SO₄. After filtration and removal of the solvent in vacuo, the crude product was purified by flash column chromatography (10% EtOAc/PE) to afford the pure product.
27 4-Fluorophenol (2a) White solid; mp 43–45 °C; 57% yield (19 mg, 0.17 mmol). ¹H NMR (200 MHz, CDCl₃): δ = 6.97–6.85 (2 H, m, ArH), 6.84–6.72 (2 H, m, ArH), 5.85 (1 H, br s, OH). ¹³C NMR (50 MHz, CDCl₃): δ = 157.3 (d, J = 237.9 Hz), 151.0 (d, J = 2.1 Hz), 116.3 (d, J = 8.1 Hz), 116.0 (d, J = 23.0). ¹⁹F NMR (188 MHz, CDCl₃): δ = -81.7. 3-Methylphenol (2e) Colorless oil; 83% yield (27 mg, 0.25 mmol). ¹H NMR (200 MHz, CDCl₃): δ = 7.18 (1 H, t, J = 8.2 Hz, ArH), 6.82 (1 H, d, J = 8.2 Hz, ArH), 6.76–6.67 (2 H, m, ArH), 6.02 (1 H, br s, OH), 2.34 (3 H, s, CH₃). ¹³C NMR (50 MHz, CDCl₃): δ = 155.0, 139.2, 129.4, 121.7, 116.1, 112.3, 21.2.

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