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Updated: Jun 22, 2026

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High-Yielding, Scalable Synthesis of 5,15-Dioxaporphyrin
Taiyou Tsutsumi1, Takanori Iwasaki1, Soji Shimizu1
1Department of Applied Chemistry, Graduate School of Engineering and Center for Molecular Systems (CMS), Kyushu University, Fukuoka 819-0395, Japan.
Abstract:
5,15-Dioxaporphyrin (DOP) is a stable 20π antiaromatic molecule with potential for investigating properties arising from antiaromaticity. However, low yields in large-scale synthesis combined with tedious workup procedures have impeded further development of DOP chemistry. Here, we established a high-yielding, scalable synthesis by modifying the concentrations, oxime reagents, reaction time, and solvents. In addition to the reasonable substrate scope, this improved method also enabled the first synthesis of a palladium complex of DOP.
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