Microwave Irradiation in Dry Media: A New and Easy Method for Synthesis of Tetrapyrrolic Compounds

Petit, Alain; Loupy, André; Maiuardb, Ph.; Momenteaub, M.

doi:10.1080/00397919208021097

Cited by 59 publications

(25 citation statements)

References 15 publications

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“…Microwave irradiation accelerates the polarization of the starting materials to promote the reactions. In comparison with previous other papers about microwave-assisted preparation of phthalocyaScheme 1. nines and porphyrin [18][19][20][21], no solvent is necessary in the reactions described in this paper and the reaction condition is mild. These advantages are paramount to fit the demand in the clean and low-cost production of soluble porphyrins and phthalocyanines.…”

Section: Microwave-assisted Processmentioning

confidence: 99%

Microwave-assisted synthesis and reverse saturable absorption of phthalocyanines and porphyrins

Liu

Tai

Wang

et al. 2004

Journal of Organometallic Chemistry

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Section: Microwave-assisted Processmentioning

confidence: 99%

Microwave-assisted synthesis and reverse saturable absorption of phthalocyanines and porphyrins

Liu

Tai

Wang

et al. 2004

Journal of Organometallic Chemistry

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“…The first report of solid-state synthesis of porphyrins under microwave radiations used silica gel, alumina, clay, and montmonillonite. According to that report, the yields were poor and not more than 10% [28].…”

Section: Resultsmentioning

confidence: 85%

Microwave‐assisted synthesis, metallation, and duff formylation of porphyrins

Yaseen

Ali

Najeebullah

et al. 2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).Microwave assisted synthesis, metallation, and b-formylation of porphyrins is described. All synthetic reactions were carried out on inorganic polymer solid support using microwave energy. It is the first documented application of the Duff reaction in the field of porphyrins and metalloporphyrins. The overall process is simple, easy, and environment friendly. FTIR, UV-visible, elemental analysis, 1 H NMR, and mass spectrometry were used to characterize the compounds.

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“…Established synthetic approaches to meso -tetrasubstituted porphyrins involve large amounts of corrosive or toxic organic solvents or high temperature reaction conditions, often followed by extensive chromatographic purification. 2-6 …”

Section: Introductionmentioning

confidence: 99%

The two-step mechanochemical synthesis of porphyrins

et al. 2014

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Porphyrin synthesis under solvent-free conditions represents the “greening” of a traditional synthesis that normally requires large amounts of organic solvent, and has hindered industrial-scale synthesis of this useful class of molecules. We have found that the four-fold acid-catalysed condensation of aldehyde and pyrrole to yield a tetra-substituted porphyrin is possible through mechanochemical techniques, without a solvent present. This represents one of the still-rare examples of carbon-carbon bond formation by mechanochemistry. Specifically, upon grinding equimolar amounts of pyrrole and benzaldehyde in presence of an acid catalyst, cyclization takes place to give reduced porphyrin precursors (reversible), which upon oxidation form tetraphenylporphyrin (TPP). The approach has been found suitable for synthesis of a variety of meso-tetrasubstituted porphyrins. Oxidation can occur either by using an oxidizing agent in solution, to give yields comparable to those published for traditional methods of porphyrin synthesis, or through mechanochemical means resulting in a two-step mechanochemical synthesis to give slightly lower yields that are still being optimized. We are also working on “green” methods of porphyrin isolation, including entrainment sublimation, which would hopefully further reduce the need for large amounts of organic solvent. These results hold promise for the development of mechanochemical synthetic protocols for porphyrins and related classes of compounds.

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Microwave Irradiation in Dry Media: A New and Easy Method for Synthesis of Tetrapyrrolic Compounds

Cited by 59 publications

References 15 publications

Microwave-assisted synthesis and reverse saturable absorption of phthalocyanines and porphyrins

Microwave-assisted synthesis and reverse saturable absorption of phthalocyanines and porphyrins

Microwave‐assisted synthesis, metallation, and duff formylation of porphyrins

The two-step mechanochemical synthesis of porphyrins

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