TBHP/TBAI-Promoted Oxidative Cyclization of o-Acylphenols for the Construction of 2-Aryloxybenzofuran-3(2H)-ones

Abstract

An efficient metal-free approach to 2-aryloxybenzofuranonefuran-3(2H)-ones has been developed. Using tert-butyl hydroperoxide as oxidant and tetrabutylammonium iodide as catalyst, 2-acylphenols reacted with phenols to provide 2-aminobenzofuran-3(2H)-one derivatives in moderate to good yields.

Key words

tert-butyl hydroperoxide - TBHP - tetrabutylammonium iodide - TBAI - benzofuran-3(2H)-one - 2-acylphenol - oxidative cyclization

• References and Notes

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• 8 Typical Experimental Procedure for the Synthesis of 2,2-Bis(4-nitrophenoxy)benzofuran-3(2H)-one (3a) In a 15 mL reaction tube a mixture of 2-acetylphenol (1a, 68 mg, 0.5 mmol), 4-nitrophenol (2a, 174 mg, 1.25 mmol), t-BuOOH (70% in H₂O, 2 mmol), TBAI (55 mg, 0.15 mol) in MeCN (2.0 mL) was stirred at r.t. under air for 16 h, until complete consumption of starting material as monitored by TLC. After the reaction was finished, the mixture was quenched with sat. Na₂S₂O₃ solution, then extracted with EtOAc, dried over anhydrous Na₂SO₄, and evaporated in vacuum. The residue was purified by flash column chromatography on silica gel (PE–EtOAc, 8:1) to give the product 3a.