Transition Metal Catalysis in Porphyrin Modifications

Averin, Alexei D.; Yakushev, Alexei A.; Beletskaya, I. P.

doi:10.6060/mhc160532a

Cited by 7 publications

(4 citation statements)

References 53 publications

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“…Our synthetic strategy to prepare macrocycles N 2 C n O x Q and N y C n Q relies on a transition metal-catalyzed macrocyclization reaction in which linear diamines with N and O atoms in the alkyl chain become linkers between two aryl residues of the quinoxaline backbone, as depicted in Scheme 1. [61][62][63] The main step of this strategy involves two consecutive Buchwald-Hartwig amination reactions performed in a one-pot fashion.…”

Section: Synthesismentioning

confidence: 99%

“…Moreover, it boasts a potentially broad substrate scope, making it promising for structure-properties studies within photophysics, sensor development, and material synthesis because the size of the macrocycle may influence its rigidity, coordinating properties, and the hydrophilic-lipophilic balance of compounds. 62 Additionally, this synthetic approach can serve as a key step in the preparation of more complex molecules that bear functional groups within the quinoxaline residue or at the aryl groups. 75…”

Section: Synthesismentioning

confidence: 99%

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Quinoxaline-based azamacrocycles: synthesis, AIE behavior and acidochromism

Kharlamova,

Ermakova,

Abel

et al. 2024

Org. Biomol. Chem.

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Section: Synthesismentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Quinoxaline-based azamacrocycles: synthesis, AIE behavior and acidochromism

Kharlamova,

Ermakova,

Abel

et al. 2024

Org. Biomol. Chem.

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“…[9][10][11] However, there is a lack of such works in the chemistry of tetrapyrrole compounds. [12][13][14][15] The only work on direct C-H borylation of tetrapyrroles was reported by Osuka et al 16 16 years ago. Bispinacolborane with iridium complex catalyst borylated mesoarylporphyrins exclusively at β-pyrrolic positions (Scheme 1a).…”

Section: Introductionmentioning

confidence: 99%

Direct C–H borylation of vinylporphyrins via copper catalysis

et al. 2022

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“…Palladium-catalyzed cross-coupling reactions are widely used to produce various functionalized derivatives of mono-and oligoporphyrins, which possess practically useful properties. [8][9][10] Most of such reactions are associated with the combination of halogenated porphyrins with various reagents. At the same time, the preparation of mono-meso-halogenated derivatives of β-alkyl substituted porphyrins is not an easy task.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Study of New N-Substituted Hydrazones of Ni(II) Complexes of β-Octaethylporphyrin and Coproporphyrin I Tetraethyl Ester

Shkirdova¹,

Zamilatskov²,

Stanetskaya³

et al. 2017

MHC

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N-Substituted hydrazones of nickel complexes of β-octaethylporphyrin and tetraethyl ester of coproporphyrin I were obtained. These compounds can serve as intermediate compounds for the preparation of meso-functionalized derivatives of porphyrins by means of various reactions. In the first stage Vilsmeier-Haack reaction was carried out by the interaction of nickel complexes of β-octaethylporphyrin and tetraethyl ester of coproporphyrin I with N,N-dimethylformamide and phosphorus(V) oxochloride forming the so-called "phosphorus complex", which was hydrolyzed with saturated solution of sodium acetate. The corresponding meso-formyl derivatives of metal porphyrins were obtained as a result. Synthesis of the hydrazones was carried out by the reactions of meso-formyl derivatives with the hydrazines using trifluoroacetic acid as a catalyst. The result of the reaction was formation of hydrazones in the form of a mixture of E-and Z-isomers, which were separated using preparative thin layer chromatography. Thus a series of hydrazoneswith different substituents at the nitrogen atom was obtained. The structures of all obtained compounds were determined using the methods of NMR spectroscopy, electronic absorption spectroscopy and mass spectrometry. For nickel complex of tosylhydrazone derivative of β-octaethylporphyrin the crystal structure was determined using X-ray diffraction. X-ray analysis shows that porphyrin molecules in the crystal form dimers bonded by two hydrogen bonds between the hydrogen atom of the NH-group of hydrazone and the oxygen atom of the sulfonate groups.

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Transition Metal Catalysis in Porphyrin Modifications

Cited by 7 publications

References 53 publications

Quinoxaline-based azamacrocycles: synthesis, AIE behavior and acidochromism

Quinoxaline-based azamacrocycles: synthesis, AIE behavior and acidochromism

Direct C–H borylation of vinylporphyrins via copper catalysis

Synthesis and Study of New N-Substituted Hydrazones of Ni(II) Complexes of β-Octaethylporphyrin and Coproporphyrin I Tetraethyl Ester

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