An Oxidant- and Catalyst-Free Electrooxidative Cross-Coupling Approach to Synthesize meso-Substituted Porphyrin Derivatives
The Journal of Organic Chemistry(2022)
摘要
The synthesis of porphyrin and chlorin derivatives has attracted significant attention due to their numerous applications. Herein, we report an environment friendly oxidant- and catalyst-free electrooxidative cross-coupling approach for multiple coupling reactions to synthesize meso C–N, C–O, and C–S substituted porphyrin and chlorin derivatives. For C–N cross-coupling reactions, diaminated porphyrins were obtained as the main products, while using 4-bromo-2,6-dimethyl aniline resulted in monoaminated product. Similarly, electrochemical catalysis of porphyrins with phenol and thiophene produced meso-disubstituted porphyrins in moderate yields under a smaller current. Chlorins were also applicable, and 20-substituted products were efficiently produced regioselectively. To the best of our knowledge, this work represents the first example of electrooxidative C–X cross-coupling of porphyrins and chlorins.
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