Functionalized heterocycle-appended porphyrins: catalysis matters.

Autor: Abdulaeva IA; A.N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS Leninsky pr., 31, building 4 Moscow 119071 Russia kirill.birin@gmail.com., Birin KP; A.N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS Leninsky pr., 31, building 4 Moscow 119071 Russia kirill.birin@gmail.com., Polivanovskaia DA; A.N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS Leninsky pr., 31, building 4 Moscow 119071 Russia kirill.birin@gmail.com., Gorbunova YG; A.N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS Leninsky pr., 31, building 4 Moscow 119071 Russia kirill.birin@gmail.com.; N.S. Kurnakov Institute of General and Inorganic Chemistry RAS Leninsky pr., 31 Moscow 119991 Russia., Tsivadze AY; A.N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS Leninsky pr., 31, building 4 Moscow 119071 Russia kirill.birin@gmail.com.; N.S. Kurnakov Institute of General and Inorganic Chemistry RAS Leninsky pr., 31 Moscow 119991 Russia.
Jazyk: angličtina
Zdroj: RSC advances [RSC Adv] 2020 Nov 23; Vol. 10 (69), pp. 42388-42399. Date of Electronic Publication: 2020 Nov 23 (Print Publication: 2020).
DOI: 10.1039/d0ra08603g
Abstrakt: The scope and limitations of the condensation of labile 2,3-diaminoporphyrin derivatives with aromatic aldehydes to provide functionalized imidazole- and pyrazine-appended porphyrins were investigated in detail. The presence of an acidic catalyst in the reaction was found to be a tool that allows the reaction path to be switched. The influence of the electronic origin of the substituents in the carbonyl components of the condensation on the yields and selectivity of the reaction was revealed. Metal-promoted cross-coupling transformations were found to be convenient for the further targeted construction of functional derivatives based on the prepared bromo-substituted pyrazinoporphyrins. Overall, these strategies provide a versatile technique for the elaboration of a variety of functionalized heterocycle-appended porphyrins for further application in the development of hybrid materials.
Competing Interests: There are no conflicts to declare.
(This journal is © The Royal Society of Chemistry.)
Databáze: MEDLINE