Aerobic alcoholization via aromatization driven C–C bond cleavage of unstrained ketones†

Abstract

Alcohols are a crucial class of organic compounds that play pivotal roles not only in organic synthesis, materials science, and industrial production but also in the pharmaceutical and agrochemical industries. Conventional methods for synthesizing alcohols typically include olefin hydration, hydroboration followed by oxidation, and reduction reactions. In this study, we report a novel aerobic aldolization approach that employs aromatization-driven C–C bond cleavage for the deacetylation of unstrained ketones. This method enables the efficient generation of various primary and secondary alcohols using oxygen gas as an environmentally friendly oxidant and reactant. The reaction does not require the use of transition-metals, acids, or bases, demonstrating excellent functional group tolerance and broad substrate scope. Notably, this method is applicable to the late-stage modification of natural products and drug molecules, highlighting its potential in synthetic and medicinal chemistry.