Following a serendipitous observation of aerobic oxidation of a dipyrromethane to dipyrromethene during a melting point observation, we have investigated the oxidation of molten bulky, aryl-substituted dipyrromethanes with air to yield dipyrromethenes. Dipyrromethenes are important precursors to porphyrins and luminescent BODIPY dyes. Deprotonated dipyrromethenes coordinate to main group and transition metals to yield new complexes that are potential catalysts for a variety of polymerization reactions and organic transformations. The synthesis of dipyrromethenes often requires oxidation of a dipyrromethane with an oxidant such as 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), which is expensive, relatively toxic, and requires more separation steps and the use of solvents to afford pure dipyrromethene. Furthermore, we have developed a high yield, one pot synthesis of BODIPY dyes starting from dipyrromethanes utilizing air oxidation. The resulting compounds have been characterized by NMR spectroscopy and high-resolution mass spectrometry. The extent of dipyrromethane conversion to dipyrromethene through air oxidation has been determined by NMR spectroscopy and isolation of pure dipyrromethene. Details of synthesis and characterization, along with the air oxidation of a series of dipyrromethanes to the corresponding dipyrromethenes will be discussed.<br/>

One- pot synthesis of BODIPY- dyes through aerobic oxidation of bulky dipyrromethanes

256th National Meeting (2018)

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