We expand the scope of our recently-discovered ortho-oxidation of 2,7-disubstituted pyrene derivatives under metal-free conditions (i.e. hypervalent iodine oxyacids HIO3 and H5IO6 in Green solvents) to include new substituents besides tert-butyl groups. In our previous report, we observed that the oxidation is sterically-driven by the effect of the tert-butyl groups. Under the same conditions that oxidized 2,7-di-tert-butylpyrene into the corresponding 4,5-dione, unsubstituted pyrene was iodinated at the most nucleophilic carbon. In this work, we investigate a variety of 2,7-disubstituted pyrenes, in which the substituents are not tert-butyl. We further demonstrate the effective dual roles hypervalent iodine oxyacids that can serve as either I-electrophiles (iodinating reagents) or O-electrophiles (oxidants).

Exploring the green oxidation and iodination of 2,7-disubstituted pyrenes

ACS Spring 2022

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