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An Oxidant- and Catalyst-Free Electrooxidative Cross-Coupling Approach to Synthesize meso-Substituted Porphyrin Derivatives

Wang, Zheng ; Cheng, Qi ; Peng, Rui-Kun ; Yan, Peng ; Zeng, Rong ; Tian, Wen-Jing ; Pan, Bin ; Gu, Jing ; Li, Yu-Long ; Ouyang, Qin

Journal of organic chemistry, 2022-04, Vol.87 (7), p.4742-4749 [Periódico revisado por pares]

United States: American Chemical Society

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  • Título:
    An Oxidant- and Catalyst-Free Electrooxidative Cross-Coupling Approach to Synthesize meso-Substituted Porphyrin Derivatives
  • Autor: Wang, Zheng ; Cheng, Qi ; Peng, Rui-Kun ; Yan, Peng ; Zeng, Rong ; Tian, Wen-Jing ; Pan, Bin ; Gu, Jing ; Li, Yu-Long ; Ouyang, Qin
  • Assuntos: Catalysis ; Oxidants ; Porphyrins
  • É parte de: Journal of organic chemistry, 2022-04, Vol.87 (7), p.4742-4749
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: 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.
  • Editor: United States: American Chemical Society
  • Idioma: Inglês
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