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Phosphonate-Substituted Pyrazinoporphyrin - a General Photocatalyst for Efficient Sulfoxidation.
Polivanovskaia, Daria A; Abdulaeva, Inna A; Birin, Kirill P; Gorbunova, Yulia G; Tsivadze, Aslan Yu.
Afiliación
  • Polivanovskaia DA; Frumkin Institute of Physical Chemistry and Electrochemistry RAS, Leninsky pr., 31, bldg. 4, Moscow, 119071, Russia.
  • Abdulaeva IA; Frumkin Institute of Physical Chemistry and Electrochemistry RAS, Leninsky pr., 31, bldg. 4, Moscow, 119071, Russia.
  • Birin KP; Frumkin Institute of Physical Chemistry and Electrochemistry RAS, Leninsky pr., 31, bldg. 4, Moscow, 119071, Russia.
  • Gorbunova YG; Frumkin Institute of Physical Chemistry and Electrochemistry RAS, Leninsky pr., 31, bldg. 4, Moscow, 119071, Russia.
  • Tsivadze AY; Kurnakov Institute of General and Inorganic Chemistry RAS, Leninsky pr., 31, Moscow, 119991, Russia.
Chempluschem ; : e202400469, 2024 Sep 11.
Article en En | MEDLINE | ID: mdl-39259034
ABSTRACT
An exceptional efficiency of pyrazine-annelated porphyrin as a general photocatalyst for the oxidation of organic sulfides is demonstrated. It is shown that phosphonate-substituted pyrazinoporphyrin 2H-1 brings together sufficient photostability and high efficiency in the aerobic photooxidation of a series of various sulfides. The influence of the reaction conditions onto the efficiency of homogeneous sulfide photooxidation in the presence of the photosensitizer (PS) was investigated and strong dependence on the solvent system was observed. The use of methanol is required for the photocatalytic sulfoxidation and the ratio of the alcohol/other solvent can significantly affect the conversion and selectivity of the reaction. The application of the prepared PS in 0.001 mol % loading allowed achieving complete conversion (97-100 %, turnover number up to 1,00,000, turnover frequency up to 6250 h-1) of substrates bearing substituents of different nature, namely aromatic and aliphatic sulfides with donor or acceptor substituents and substituents prone to oxidation, as well as cyclic sulfides. The selectivity of the of the corresponding sulfoxides formation of 96-100 % was revealed. Finally, a gram-scale synthesis of several sulfoxides was successfully performed with the PS under investigation, providing desired products in 66-96 % yield with over 98 % purity.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chempluschem Año: 2024 Tipo del documento: Article País de afiliación: Rusia Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chempluschem Año: 2024 Tipo del documento: Article País de afiliación: Rusia Pais de publicación: Alemania