A Brief on Thiocyanation of N-Activated Arenes and N-Bearing Heteroaromatic Compounds

doi:10.7598/cst2013.386

Cited by 3 publications

(3 citation statements)

References 32 publications

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“…A unique reaction has been designed, in which corrole acts as a self-catalyst and introduces four thiocyanato groups in the β-pyrrolic positions and thus resulted in the formation of tetrathiocyanatocorroles. It is well-known that the thiocyanate motif is a potential building block in organic chemistry as it is the precursor of a host of sulfur-containing functional groups (e.g., sulfides, thioesters, and thiophenols) and also acts as a starting material of various heterocyclic compounds (e.g., thiazoles). , Visible light-induced thiocyanation has recently gained ground to synthesize various thiocyanato appended arenes and heterocycles. − Thus, these thiocyanato appended corroles will act as possible precursors for the synthesis of several sulfur-containing corrole derivatives and which will have potential implication in dyes and drugs. It was also observed that the β-substitutions at the corrole ring has a pronounced effect on its electronic structure. − …”

Section: Introductionmentioning

confidence: 99%

Photocatalytic C–H Thiocyanation of Corroles: Development of Near-Infrared (NIR)-Emissive Dyes

et al. 2021

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A new method of activating corrole macrocycles via an in situ generated SCN radical has been developed at very mild conditions at room temperature. This photoredox reaction resulted in the generation of tetrathiocyanatocorroles in good yields. The synthesis of tetrathiocyanatocorroles was never reported earlier. Single-crystal XRD analysis reveals that the insertion of four thiocyanate moieties at the four β-pyrrolic positions has imparted significant distortion to the corrole macrocycle. The generated tetrathiocyanatocorroles are different from the parent corroles in many ways. The photophysical properties of the newly synthesized tetrathiocyanatocorroles are dramatically altered from the parent corroles. The absorption feature of these modified corrole derivatives (both position and intensity) bears a nice similarity with the chlorophyll-a macrocycle. Thus, these newly synthesized molecules can be considered as spectroscopic model systems for chlorophyll-a pigments. The observed absorption and emission spectra of these tetrathiocyanatocorroles certainly point out that these newly developed ligand scaffolds and their various metal complexes will have immense potential as pigments in solar cells and also as NIR-emissive dyes. The observed C-H•••Au weak interactions in a representative Au(III)-corrole complex point out that these complexes are capable of activating the unfunctionalized C−H groups and thus will have potential implications in C-H activation reactions.

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Section: Introductionmentioning

confidence: 99%

Photocatalytic C–H Thiocyanation of Corroles: Development of Near-Infrared (NIR)-Emissive Dyes

et al. 2021

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“…Our attention was attracted by C-H thiocyanation of (hetero)arenes, which is usually carried out chemically [8,9]. Resulting (hetero)aryl thiocyanates are interesting as precursors of various sulfur-containing compounds, as well as substances with a wide spectrum of bioactivity [8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, that C-H (An) thiocyanation can be carried out at galvanostatic electrolysis (GE) [14,16,[19][20][21]. The key intermediate of such processes is well-known [8,9] thiocyanogen (I ), which is electrogenerated at stage I → I . In addition to interaction with arene II, leading to aryl thiocyanate III (stage (I + II → III), thiocyanogen I is capable of polymerization to polythiocyanogen IV (stage I → IV) [14,16,22].…”

Section: Introductionmentioning

confidence: 99%

A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines

et al. 2020

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In this article, we demonstrate how an original effective “metal-free” and “chromatography-free” route for the synthesis of 3-thiocyanatopyrazolo[1,5-a]pyrimidines has been developed. It is based on electrooxidative (anodic) C–H thiocyanation of 5-aminopyrazoles by thiocyanate ion leading to 4-thiocyanato-5-aminopyrazoles (stage 1, yields up to 87%) following by their chemical condensation with 1,3-dicarbonyl compounds or their derivatives (stage 2, yields up to 96%). This method is equally effective for the synthesis of 3-thiocyanatopyrazolo[1,5-a]pyrimidines, both without substituents and with various donor (acceptor) substituents in the pyrimidine ring.

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Electrooxidation Is a Promising Approach to Functionalization of Pyrazole-Type Compounds

et al. 2021

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The review summarizes for the first time the poorly studied electrooxidative functionalization of pyrazole derivatives leading to the C–Cl, C–Br, C–I, C–S and N–N coupling products with applied properties. The introduction discusses some aspects of aromatic hydrogen substitution. Further, we mainly consider our works on effective synthesis of the corresponding halogeno, thiocyanato and azo compounds using cheap, affordable and environmentally promising electric currents.

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A Brief on Thiocyanation of N-Activated Arenes and N-Bearing Heteroaromatic Compounds

Cited by 3 publications

References 32 publications

Photocatalytic C–H Thiocyanation of Corroles: Development of Near-Infrared (NIR)-Emissive Dyes

Photocatalytic C–H Thiocyanation of Corroles: Development of Near-Infrared (NIR)-Emissive Dyes

A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines

Electrooxidation Is a Promising Approach to Functionalization of Pyrazole-Type Compounds

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