A Mild and Highly Efficient Conversion of Arylboronic Acids into Phenols by Oxidation with MCPBA

Abstract

A mild and highly efficient synthesis of phenols from arylboronic acids in a H₂O–EtOH (1:2) solution was achieved by using MCPBA as the oxidant at room temperature. Isotopical labeling studies had shown that the hydroxyl oxygen atom of the phenol might originate from the MCPBA.

Key words

arylboronic acids - efficiency - MCPBA - oxidation - phenols

• References and Notes

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• 7 General Procedure for the Hydroxylation of Phenylboronic Acid To the mixture of phenylboronic acid (0.5 mmol) in a H₂O–EtOH (1:2) solution (2 mL) in a round-bottom flask was added MCPBA (0.5 mmol) at r.t. When phenylboronic acid was completely consumed (monitored by TLC, 6 h), 0.1 M aq NaHCO₃ (5 mL) was added to the mixture. Then the reaction mixture was extracted with EtOAc (2 × 15 mL). The combined organic layer was washed with H₂O (10 mL) and brine (5 mL), dried over anhyd MgSO₄, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (PE–EtOAc = 4:1), and the corresponding phenol was obtained as a colorless solid (2a, 46 mg, 97%).