Metal‐free Dehydrogenation of Substituted Cyclohexanones to Phenols

Abstract

AbstractThe preparation of substituted phenols via a direct carbonyl desaturation is an intrinsic challenging task in modern synthetic chemistry. Herein, we develop a modular catalytic protocol for the synthesis of substituted phenols via the direct dehydrogenative aromatization of simple cyclohexanones in a metal‐free manner. A broad variety of substrates bearing an assortment of functional substituent groups are compatible with this protocol. Preliminary mechanistic investigations revealed that the reaction underwent a hydride leaving mechanism in the presence of a catalytic amount of tetrabutylammonium iodide. The current approach features simple operation, low reagent cost and green conditions. Insight gained from our studies is expected to advance general efforts towards the green synthesis of structurally diverse phenols via readily available raw materials, offering an alternative strategy for the carbonyl desaturation in organic synthesis.magnified image