MTO/H2O2/Pyrazole-Mediated N-Oxidation of meso-Tetraarylporphyrins and -chlorins, and S-Oxidation of a meso-Tetraaryldithiaporphyrin and -chlorin

Banerjee, Subhadeep; Zeller, Mat­thias; Brückner, Christian

doi:10.1021/jo9005443

Cited by 21 publications

(39 citation statements)

References 44 publications

(61 reference statements)

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“…Oxygenation of porphyrin 30a and dithiaporphyrin 32. 87 Matano and co-workers reported the oxygenation of phosphaporphyrins [88][89][90][91] The oxidation of N-confused porphyrin yielding a framework with a tetrahedral inner C (21) carbon atom was also described for free base 1b. 102 The oxidative addition of alcohol to 1b Scheme 23.…”

Section: Oxygenation Of Heteroporphyrins and X-confused Porphyrinsmentioning

confidence: 99%

Core chemistry and skeletal rearrangements of porphyrinoids and metalloporphyrinoids

2015

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Core alteration, affording heteroporphyrinoids and carbaporphyrinoids, allows for the exploration of porphyrin-like or porphyrin-unlike coordination chemistry. Such a strategy has provided a fundamental change in the approach to macrocyclic organometallic chemistry. The specific reactivity of porphyrinoids has offered an insight into reactions inside particularly shaped macrocyclic architecture, including metal-mediated organic transformations. This review focuses on alterations of macrocycles, made of four carbocyclic/heterocyclic subunits, which resemble the structure of porphyrin or porphyrin isomers, providing, however, remarkable porphyrin-like (XNNN), (CNNN), (CNCN) or (C2NNN) surroundings. To facilitate the understanding of the discussed subject matter, all addressed reactions reflecting core reactivity have been formally grouped into nine categories distinguished by the principal type of transformation addressed: (1) alkylation or arylation, (2) core heteroatom replacement, (3) oxidation and oxygenation, (4) substitution, (5) macrocyclic fusion, (6) core bridging, (7) ring contraction, (8) ring expansion, and (9) C-H and C-C bond activation. The distinctive macrocyclic environment creates a long-sought opportunity to trap unique organometallic transformations which include instances of benzene ring contraction to cyclopentadiene or the formation of an unprecedented metalloporphyrinoid: 21-pallada-23-telluraporphyrin. This review offers certain challenging perspectives which target the goals of organometallic bond activation.

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Section: Oxygenation Of Heteroporphyrins and X-confused Porphyrinsmentioning

confidence: 99%

Core chemistry and skeletal rearrangements of porphyrinoids and metalloporphyrinoids

2015

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“…The methyltrioxorhenium (MTO)-catalyzed H 2 O 2 oxidation of the 2,3-dioxochlorin 44 , in the presence of pyrazole, leads to the formation of four pyrrole-modified porphyrin derivatives (Scheme 17) [55,70]. During the reaction course it is observed the initial formation of compounds 45 and 5 while the corresponding N -oxides 47 and 48 are formed later in the reaction, and on the expense of the products formed initially [55].…”

Section: Chemistrymentioning

confidence: 99%

Porphyrin Macrocycle Modification: Pyrrole Ring-Contracted or -Expanded Porphyrinoids

Costa

Tomé

2016

Molecules

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Abstract:In recent years, several synthetic strategies aiming at the peripheral functionalization of porphyrins were developed. Particularly interesting are those involving the modification of β-pyrrolic positions leading to pyrrole-modified porphyrins containing four-, five-, six-or seven-membered heterocycles. Azeteoporphyrins, porpholactones and morpholinoporphyrins are representative examples of such porphyrinoids. These porphyrin derivatives have recently gained an increasing interest due to their potential application in PDT, as multimodal imaging contrast agents, NIR-absorbing dyes, optical sensors for oxygen, cyanide, hypochlorite and pH, and in catalysis.

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“…Peripheral oxidation transformation is a very popular approach for preparation of asymmetric functionalized porphyrins, [244][245][246][247][248][249][250][251][252][253][254][255] but so far has only limited application in phthalocyanine chemistry. Thus, octa(dimethylamino)-substituted tetraazaporphyrins 79 can be oxidized by manganese(IV) oxide to form two different seco-porphyrazines 80 and 81 (Scheme 27A).…”

Section: Oxidative Transformation Strategymentioning

confidence: 99%

Synthetic approaches to asymmetric phthalocyanines and their analogues

Nemykin¹,

Dudkin²,

Dumoulin³

et al. 2014

Arkivoc

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This review summarizes synthetic strategies for the preparation of asymmetric phthalocyanines and their analogues. Cross-condensation between two phthalonitrile components, crosscondensation between one phthalonitrile and one non-nitrile component, targeted synthesis of AABB-type compounds, the subphthalocyanine ring-expansion method, as well as postmodification approaches on pre-formed symmetric and asymmetric systems, are discussed. Methodologies for targeted preparation of specific types of asymmetric phthalocyanines and their analogues are also briefly overviewed.

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MTO/H₂O₂/Pyrazole-Mediated N-Oxidation of meso-Tetraarylporphyrins and -chlorins, and S-Oxidation of a meso-Tetraaryldithiaporphyrin and -chlorin

Cited by 21 publications

References 44 publications

Core chemistry and skeletal rearrangements of porphyrinoids and metalloporphyrinoids

Core chemistry and skeletal rearrangements of porphyrinoids and metalloporphyrinoids

Porphyrin Macrocycle Modification: Pyrrole Ring-Contracted or -Expanded Porphyrinoids

Synthetic approaches to asymmetric phthalocyanines and their analogues

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