The oxidation of alcohols into aldehydes and ketones is a fundamental transformation in synthetic organic chemistry, as these products serve as versatile functional handles for further functionalization of organic molecules. This makes oxidation reactions extremely useful in organic synthesis of either reactive intermediates or target products. However, forming more reactive carbonyl moieties such as 1,3-diones has proven difficult through oxidation alone. It is shown here that through the tandem oxidation and nucleophilic coupling of two alcohol starting materials, 1,3-diketone functionalities can be synthesized in a one-pot method through the oxidation of a reactive intermediate. By coupling multiple transformations, we can capture and functionalize reaction components too sensitive to be isolated, allowing for the conversion of simple functional groups to more useful moieties in a single step. The utility and efficiency of this transformation is highlighted by the ready availability of the starting materials, including the oxidant which is generated <i>in situ</i> from ambient oxygen. The development of this method shows potential for future expansion of substrate scope as well as the elucidation and understanding of the mechanism through which this transformation occurs.

Tandem oxidation and dehydrogenative-coupling for the rapid synthesis of 1,3-diones

2019 Spring National Meeting

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