A Survey of Acid Catalysts for Use in Two-Step, One-Flask Syntheses of Meso-Substituted Porphyrinic Macrocycles

Gr, Geier; Ciringh, Yangzhen; F, Li; Dm, Haynes; Js, Lindsey

doi:10.1021/ol005917h

Cited by 88 publications

(62 citation statements)

References 21 publications

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“…One seminal contribution along these lines was made in 1995 when LatosGrazyń ski and co-workers reported that tetraphenylsapphyrin can be obtained in 1.1 % yield by condensing pyrrole and benzaldehyde under appropriate conditions. [70] Subsequent efforts by Lindsey and co-workers to optimize the synthesis of N-confused porphyrin (obtained in remarkable yields up to 40 %), [79] failed to improve the yield of tetraphenylsapphyrin obtained from this reaction (namely, the direct condensation of pyrrole and benzaldehyde). Indeed, the maximum yield obtained by Lindsey and coworkers was 1.2 %.…”

Section: New Advances In the Area Of Sapphyrin Chemistrymentioning

confidence: 99%

Synthetic Expanded Porphyrin Chemistry

2003

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Expanded porphyrins are synthetic analogues of the porphyrins, and differ from these and other naturally occurring tetrapyrrolic macrocycles by containing a larger central core with a minimum of 17 atoms, while retaining the extended conjugation features that are a hallmark of these quintessential biological pigments. The result of core expansion is to produce systems with novel spectral and electronic features, interesting and, often unprecedented, cation-coordination properties, and, in many cases, an ability to bind anions in certain protonation states. Also adding to the appeal of expanded porphyrins is their central role in addressing issues of aromaticity. In many cases, they also display structural features, such as decidedly nonplanar "figure-eight" motifs, that have no antecedents in the chemistry of porphyrins or related macrocyclic compounds. In this Review, the various synthetic approaches now being employed to produce expanded porphyrins as well as their various applications-related aspects are discussed.

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Section: New Advances In the Area Of Sapphyrin Chemistrymentioning

confidence: 99%

Synthetic Expanded Porphyrin Chemistry

2003

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“…Chemists have developed a few synthetic methods to provide convenient access to synthesize substituent tetraphenylporphyrin complexes [9][10][11]. The prevalent method of synthesis involves a mixed aldehyde condensation with pyrrole via Adler method in refluxing propionic acid [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of p-substituted tetraphenylporphyrins and corresponding ferric complexes with mixed-solvents method

Sun

She

Zhong

2009

Front. Chem. Eng. China

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By using mixed-solvents method, five kinds of p-substituted tetraphenylporphyrin compounds [T(p-R)PPH 2 , R = NO 2 , Cl, CH 3 , OCH 3 , OH] were synthesized by the condensation of p-substituted benzaldehyde with pyrrole in mixed solvents (propionic acid, acetic acid and nitrobenzene), and corresponding ferric complexes [T(p-R)PPFe III Cl] were synthesized in dimethylformamide. The above free base porphyrins were obtained in 30%-50% yields, metalation yields were up to 90% and total yields of ferric complexes were 27%-50%. Effects of reactive conditions, solvents and oxidants on yields of free base porphyrins were investigated and the relevant mechanism was discussed. Structures of the above porphyrin complexes were characterized by ultravioletvisible (UV-Vis), infrared (IR) and far infrared (FIR) spectroscopy.

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“…[30][31][32] Above all, the synthetic methods of TPPH 2 in the single solvent or solvent-free systems have been widely developed in recent years. [33][34][35] However, the present synthesis of TPPH 2 from the direct condensation of benzaldehyde and pyrrole is still inconvenient and the purity of products directly separated from the filtrate remains to be improved. In our previous reports, 36,37 the synthesis of para-substituted tetraphenylporphyrins with the mixed-solvent method was developed on the research basis of Gonsalves.…”

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confidence: 99%

Synthesis of substituted meso-tetraphenylporphyrins in mixed solvent systems

Sun¹,

She²,

Cao³

et al. 2013

Arkivoc

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An efficient synthetic method of substituted meso-tetraphenylporphyrins with better isolated yields was proposed by using propionic acid, valeric acid and m-nitrotoluene as mixed-solvent systems. The porphyrin yields in mixed solvent systems were obviously higher than those in the single propionic acid or valeric acid as solvents. The further investigation showed that the acidity, polarity, viscosity and the property of oxidant played an important role to the synthesis of porphyrin. Compared with other oxidants, m-nitrotoluene as an excellent oxidant could completely transform tetraphenylporphyrinogen to tetraphenylporphyrin.

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A Survey of Acid Catalysts for Use in Two-Step, One-Flask Syntheses of Meso-Substituted Porphyrinic Macrocycles

Cited by 88 publications

References 21 publications

Synthetic Expanded Porphyrin Chemistry

Synthetic Expanded Porphyrin Chemistry

Synthesis of p-substituted tetraphenylporphyrins and corresponding ferric complexes with mixed-solvents method

Synthesis of substituted meso-tetraphenylporphyrins in mixed solvent systems

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