New syntheses and reactions of some halogenated porphyrins

Minnetian, Ohannes M.; Morris, Ian K.; Snow, Kevin M.; Smith, Kevin M.

doi:10.1021/jo00284a033

Cited by 36 publications

(17 citation statements)

References 4 publications

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“…Stille-type reactions were first used in porphyrin functionalization for the preparation of protoporphyrin IX dimethyl ester 98 from dibromo-deuteroporphyrin IX dimethyl ester 97 in 85% yield (Scheme 33 ) [87]. …”

Section: Porphyrin Functionalizationmentioning

confidence: 99%

Syntheses and Functionalizations of Porphyrin Macrocycles

Vicente¹,

Smith²

2014

COS

110

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Porphyrin macrocycles have been the subject of intense study in the last century because they are widely distributed in nature, usually as metal complexes of either iron or magnesium. As such, they serve as the prosthetic groups in a wide variety of primary metabolites, such as hemoglobins, myoglobins, cytochromes, catalases, peroxidases, chlorophylls, and bacteriochlorophylls; these compounds have multiple applications in materials science, biology and medicine. This article describes current methodology for preparation of simple, symmetrical model porphyrins, as well as more complex protocols for preparation of unsymmetrically substituted porphyrin macrocycles similar to those found in nature. The basic chemical reactivity of porphyrins and metalloporphyrin is also described, including electrophilic and nucleophilic reactions, oxidations, reductions, and metal-mediated cross-coupling reactions. Using the synthetic approaches and reactivity profiles presented, eventually almost any substituted porphyrin system can be prepared for applications in a variety of areas, including in catalysis, electron transport, model biological systems and therapeutics.

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Section: Porphyrin Functionalizationmentioning

confidence: 99%

Syntheses and Functionalizations of Porphyrin Macrocycles

Vicente¹,

Smith²

2014

COS

110

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“…of Br 2 substitution takes place first at the mercurated β-positions, and meso-bromination then takes place if the concentration of bromine is increased. Coupling of the zinc deuteroporphyrinate-IX with 1,2-dibromopropene leads to a mixture containing 8% each of the monobrominated deuteroporphyrins 20 and 20% of the dibrominated deuteroporphyrinate 21 [18]. These difficulties were overcome by means of bromination.…”

Section: β-Polyalkylporphyrinsmentioning

confidence: 99%

Bromination of porphyrins (Review)

Chumakov

Khoroshutin

Anisimov

et al. 2009

Chem Heterocycl Comp

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“…Recent publications have described some impressive examples using this strategy, utilizing synthetic tetraphenyl-substituted porphyrin precursors which were linked by ethinyl and butadiinyl units to give up to pentameric units via Heck-type reactions [1] . In contrast only very few examples exploiting the natural tetrapyrrole derivatives are known [3] [15] . Although these substances are much more interesting, due to their similarity to systems found in nature, they are more difficult to handle due to the additional functional groups which can lead to undesirable side reactions.…”

mentioning

confidence: 99%