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Paper | Special issue | Vol 95, No. 2, 2017, pp.1132-1147
Published online, 31st January, 2017
DOI: 10.3987/COM-16-S(S)84
Ammonium Hypoiodite-Catalyzed Peroxidative Dearomatization of Phenols

Muhammet Uyanik, Kohei Nishioka, and Kazuaki Ishihara*

*Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8603, Japan

Abstract

Here, we report the first transition metal-free peroxidative dearomatization of phenols using hypoiodite catalysis with TBHP. Hypoiodite salts are generated in situ from the corresponding quaternary ammonium iodides in the presence of TBHP, and the oxidative coupling reaction proceeds efficiently under mild conditions. The dearomatized products are versatile synthetic intermediates for further synthetic transformations to various complex structures including heterocycles. As a demonstration, the further oxidation of the unsaturated peroxide with TBHP afforded the corresponding peroxy epoxide in good yield.