Iridium Complex of N‐Fused Bilatrienone: Oxidative Cleavage of N‐Fused Porphyrin Induced by Iridium‐Cyclooctadiene Complexation

Abraham, Jibin Alex; Mori, Shigeki; Ishida, Masatoshi; Furuta, Hiroyuki

doi:10.1002/chem.202100789

Cited by 7 publications

(6 citation statements)

References 43 publications

(39 reference statements)

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“…Although oxidative ring-opening reactions for porphyrins and the related macrocycles have been reported, the degradation of the corrorin appended porphyrinoids has not been explored, to the best of our knowledge. Theoretically, there are four possible ring-cleavage modes (Figure ), but 2 was obtained as the sole regioselective product.…”

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confidence: 99%

Confusion Approach Modulated Syntheses of Corrorin Parasitized Hexaphyrins(1.1.1.1.1.0) and the Oxidative Ring Cleavage Behavior

Zhu

et al. 2021

Org. Lett.

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A corrorin parasitized hexaphyrin(1.1.1.1.1.0) 1 was synthesized by [4 + 4] condensation, and subsequent treatment with PbO 2 afforded hexaphyrin 2 appended with a dipyrrinone moiety via regioselective opening of the corrorin ring. In contrast, oxidation of the corresponding corrorin−Nconfused hexaphyrin(1.1.1.1.1.0) hybrid 3 afforded only a keto adduct 4. As a result, the planarity and aromaticity of the hexaphyrin moiety can be modulated.

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confidence: 99%

Confusion Approach Modulated Syntheses of Corrorin Parasitized Hexaphyrins(1.1.1.1.1.0) and the Oxidative Ring Cleavage Behavior

Zhu

et al. 2021

Org. Lett.

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“…[60] N-fused bilatrienones such as 17, on the other hand, can be obtained from 16 and the iridium complex in Scheme 11, where 1,5-cod is a shorthand for cyclooctane-1,5diene. [61]…”

Section: From N-confused and N-fused Porphyrinsmentioning

confidence: 99%

Making and Breaking Helical Open‐Chain Oligopyrroles

Urban,

De Feyter

2024

ChemPlusChem

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Closed‐chain oligopyrroles such as porphyrins or corroles have been well‐established in literature and experience a steadily strong interest by several fields of science. However, their open‐chain derivatives are comparatively underrepresented, despite their intriguing properties and promising applications. Here, we aim to review typical synthetic routes, as well as point towards several emergent properties, marking them as interesting candidates for various fields of study. The review focuses on two traditional methods (each starting from highly symmetric metalloporphyrins) and then expands its scope towards more recent variations before moving on to more exotic and recent highlights that have yet to be included into the canon. Key chemical reactivities (ring closure, substitution and fragmentation) are then followed by notable physicochemical properties, placing special emphasis on potential uses in molecular electronics and sensors.

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“…In a similar reaction of NFTPP with [Ir(OMe)(COD)] 2 under argon atmosphere, an equimolar amount of NFP iridium(III) complexes 323a and 323b was obtained in 61% combined yield (Scheme ). Here, isomerization between 323a and 323b was not recognized even at elevated temperatures. Interestingly, when the same reaction was examined in air, oxidative ring-opening of the NFP ligand was observed together with oxidation of the COD ligand to give the iridium(III) complex of N-fused bilatrienone 324 and NFP iridium(III) complexes 325a – b in 37% and 12% yields, respectively (Scheme ).…”

Section: N-fused Porphyrinsmentioning

confidence: 99%

Creation from Confusion and Fusion in the Porphyrin World─The Last Three Decades of N-Confused Porphyrinoid Chemistry

Toganoh

Furuta

2022

Chem. Rev.

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Confusion is a novel concept of isomerism in porphyrin chemistry, delivering a steady stream of new chemistry since the discovery of N-confused porphyrin, a porphyrin mutant, in 1994. These days, the number of confused porphyrinoids is increasing, and confusion and associated fusion are found in various fields such as supramolecular chemistry, materials chemistry, biological chemistry, and catalysts. In this review, the birth and growth of confused porphyrinoids in the last three decades are described.

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Iridium Complex of N‐Fused Bilatrienone: Oxidative Cleavage of N‐Fused Porphyrin Induced by Iridium‐Cyclooctadiene Complexation

Cited by 7 publications

References 43 publications

Confusion Approach Modulated Syntheses of Corrorin Parasitized Hexaphyrins(1.1.1.1.1.0) and the Oxidative Ring Cleavage Behavior

Confusion Approach Modulated Syntheses of Corrorin Parasitized Hexaphyrins(1.1.1.1.1.0) and the Oxidative Ring Cleavage Behavior

Making and Breaking Helical Open‐Chain Oligopyrroles

Creation from Confusion and Fusion in the Porphyrin World─The Last Three Decades of N-Confused Porphyrinoid Chemistry

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