Synthesis of 2-benzoylpyrrole derivatives via C–H functionalization adjacent to nitrogen of pyrrole

Wei, Xuehong; Hua, Yupeng; Chao, Jianbin; Liu, Dian‐Sheng

doi:10.1016/j.tetlet.2015.04.118

Cited by 12 publications

(8 citation statements)

References 34 publications

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“…With the purpose of obtaining efficient TTA‐UC sensitizers, the asymmetric BODIPY derivatives, B2P and B2PI, shown in Scheme 2 were prepared according to Scheme 3. The first step was the synthesis of the ketopyrrole 1 , following a procedure modified from literature [38] …”

Section: Resultsmentioning

confidence: 99%

“…The first step was the synthesis of the ketopyrrole 1, following a procedure modified from literature. [38] We then carried out the halogenation of 1 using Br 2 . Both steps were successfully optimized to avoid chromatography (isolation was by crystallization) and afforded the products in high purity and yield.…”

Section: Synthesis Of the Dyadsmentioning

confidence: 99%

“…Synthesis of 1: Ketopyrrole 1 was prepared following a modified reported procedure. [38] In a 100 mL round bottom flask 2,4-dimethylpyrrole (2 mL, 19.42 mmol) was dissolved in 30 mL of diethyl ether at 0 °C in an ice/water bath, n-BuLi 2.5 M in hexanes was added dropwise (8.55 mL, 21.37 mmol, 1.1 equiv.) and the bath was removed.…”

Section: Synthesis Of B2pmentioning

confidence: 99%

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BODIPY‐Perylene Charge Transfer Compounds; Sensitizers for Triplet‐Triplet Annihilation Up‐conversion

Arellano-Reyes

Prabhakaran

Sia

et al. 2023

Chemistry A European J

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BODIPY heterochromophores, asymmetrically substituted with perylene and/or iodine at the 2 and 6 positions were prepared and investigated as sensitizers for triplet‐triplet annihilation up conversion (TTA‐UC). Single‐crystal X‐ray crystallographic analyses show that the torsion angle between BODIPY and perylene units lie between 73.54 and 74.51, though they are not orthogonal. Both compounds show intense, charge transfer absorption and emission profiles, confirmed by resonance Raman spectroscopy and consistent with DFT calculations. The emission quantum yield was solvent dependent but the emission profile remained characteristic of CT transition across all solvents explored. Both BODIPY derivatives were found to be effective sensitizers of TTA‐UC with perylene annihilator in dioxane and DMSO. Intense anti‐Stokes emission was observed, and visible by eye from these solvents. Conversely, no TTA‐UC was observed from the other solvents explored, including from non‐polar solvents such as toluene and hexane that yielded brightest fluorescence from the BODIPY derivatives. In dioxane, the power density plots obtained were strongly consistent with TTA‐UC and the power density threshold, the Ith value (the photon flux at which 50 % of ΦTTAUC is achieved), for B2PI was observed to be 2.5x lower than of B2P under optimal conditions, an effect ascribed to the combined influence of spin‐orbit charge transfer intersystem crossing (SOCT‐ISC) and heavy metal on the triplet state formation for B2PI.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of the Dyadsmentioning

confidence: 99%

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BODIPY‐Perylene Charge Transfer Compounds; Sensitizers for Triplet‐Triplet Annihilation Up‐conversion

Arellano-Reyes

Prabhakaran

Sia

et al. 2023

Chemistry A European J

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“…To obtain monochlorinated BODIPYs, it was first converted into the respective 2-benzoylpyrrole 2 for the meso aryl examples. 10 TBS protection of the benzyl alcohol byproduct in the crude product simplified the purification later on. 11 This species and 2-acetylpyrrole were then chlorinated using NCS in THF at room temperature to obtain α-chlorinated 2-acylpyrroles 3 and 4.…”

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confidence: 99%

Linear Amine-Linked Oligo-BODIPYs: Convergent Access via Buchwald–Hartwig Coupling

Röttger,

Patalag,

Hasenmaile

et al. 2024

Org. Lett.

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A convergent route toward nitrogen-bridged BODIPY oligomers has been developed. The synthetic key step is a Buchwald−Hartwig cross-coupling reaction of an α-amino-BODIPY and the respective halide. Not only does the selective synthesis provide control of the oligomer size, but the facile preparative procedure also enables easy access to these types of dyes. Furthermore, functionalized examples were accessible via brominated derivatives.

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“…as tags for bioimaging or as photosensitizers for various substrates. 3 Aromatic azo compounds, derived from azobenzene, which was first reported by Mitscherlich, 4 constitute another class of dyes. They too find a variety of applications, e.g.…”

mentioning

confidence: 99%

Phenylazo-BODIPYs: Direct Access via Pd-Catalysis

Werz,

Röttger,

Birk

et al. 2024

Synlett

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Synthesis of 2-benzoylpyrrole derivatives via C–H functionalization adjacent to nitrogen of pyrrole

Cited by 12 publications

References 34 publications

BODIPY‐Perylene Charge Transfer Compounds; Sensitizers for Triplet‐Triplet Annihilation Up‐conversion

BODIPY‐Perylene Charge Transfer Compounds; Sensitizers for Triplet‐Triplet Annihilation Up‐conversion

Linear Amine-Linked Oligo-BODIPYs: Convergent Access via Buchwald–Hartwig Coupling

Phenylazo-BODIPYs: Direct Access via Pd-Catalysis

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