Base-Promoted, Mild and Highly Efficient Conversion of Arylboronic Acids into Phenols with tert-Butyl Hydroperoxide

Abstract

A mild and efficient protocol for the synthesis of phenols from arylboronic acids has been developed by using tert-butyl ­hydroperoxide with base as promoter. The corresponding phenols were obtained in good to excellent yields within several minutes.

Key words

arylboronic acid - phenol - peroxides - base - synthetic methods

• References and Notes

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• 24 Preparation of 2; General Procedure: A mixture of arylboronic acid (1.0 mmol), KOH (112 mg, 2.0 mmol), H₂O (2.0 mL), and 70% TBHP (0.3 mL) was stirred at r.t. for 10 min. The reaction was monitored by TLC analysis. Upon completion, the reaction mixture was washed with 1 M HCl (2 mL) and extracted with EtOAc (3 × 15 mL). The organic phase was concentrated and the resulting crude product was purified by column chromatography on silica gel (petroleum ether–EtOAc, 20:1) to provide the desired compound; the product was characterized by GC-MS and NMR spectroscopy.