Iron-promoted one-pot approach: Synthesis of isothiocyanates

Pendem, Venkata Bhavanarushi; Madhavi, N.

doi:10.1080/10426507.2020.1716755

Cited by 13 publications

(8 citation statements)

References 44 publications

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“…160 °C but then rapidly decomposes. The isolation and relatively high temperature decomposition of [Fe(S 2 CNHPh) 3 ] is not in accord with recent work by Nannapaneni, which shows that [PhNHCS 2 ][Et 3 NH] decomposes at room temperature in the presence of FeCl 3 , 144 although we note that the reaction was carried out in the presence of base (NEt 3 ). This transformation is found for a wide range of anilines and also some aliphatic secondary amines, suggesting that complexes of the type [Fe(S 2 CNHR) 3 ] may be useful precursors for the low temperature formation of iron sulfides.…”

Section: Groupcontrasting

confidence: 70%

“…400 °C, the latter being the reason why these complexes are not used for the deposition of thin films of HgS. Clearly, in solution, another process dominates, possibly an intramolecular ligand to metal electron-transfer, to generate TDS and a Hg(I) complex, akin to the thermally induced electron-transfer seen for [Fe(S 2 CNR 2 ) 3 ]. , Such a process might be expected to be light activated. Mercury(I) DTCs are unknown, and thus this initial electron transfer may trigger a catastrophic decomposition to afford HgS.…”

Section: Binary Sulfidesmentioning

confidence: 99%

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Dithiocarbamate Complexes as Single Source Precursors to Nanoscale Binary, Ternary and Quaternary Metal Sulfides

2021

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Nanodimensional metal sulfides are a developing class of low-cost materials with potential applications in areas as wide-ranging as energy storage, electrocatalysis, and imaging. An attractive synthetic strategy, which allows careful control over stoichiometry, is the single source precursor (SSP) approach in which well-defined molecular species containing preformed metal–sulfur bonds are heated to decomposition, either in the vapor or solution phase, resulting in facile loss of organics and formation of nanodimensional metal sulfides. By careful control of the precursor, the decomposition environment and addition of surfactants, this approach affords a range of nanocrystalline materials from a library of precursors. Dithiocarbamates (DTCs) are monoanionic chelating ligands that have been known for over a century and find applications in agriculture, medicine, and materials science. They are easily prepared from nontoxic secondary and primary amines and form stable complexes with all elements. Since pioneering work in the late 1980s, the use of DTC complexes as SSPs to a wide range of binary, ternary, and multinary sulfides has been extensively documented. This review maps these developments, from the formation of thin films, often comprised of embedded nanocrystals, to quantum dots coated with organic ligands or shelled by other metal sulfides that show high photoluminescence quantum yields, and a range of other nanomaterials in which both the phase and morphology of the nanocrystals can be engineered, allowing fine-tuning of technologically important physical properties, thus opening up a myriad of potential applications.

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Section: Groupcontrasting

confidence: 70%

Section: Binary Sulfidesmentioning

confidence: 99%

Dithiocarbamate Complexes as Single Source Precursors to Nanoscale Binary, Ternary and Quaternary Metal Sulfides

2021

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“…Ltd. and was used without further purification. Phenyl isothiocyanates were prepared from anilines as per the reported procedure with few modifications . Column chromatography was performed using silica gel (60–120 mesh) acquired from SRL Pvt.…”

Section: Methodsmentioning

confidence: 99%

“…Phenyl isothiocyanates were prepared from anilines as per the reported procedure with few modifications. 17 Column chromatography was performed using silica gel (60−120 mesh) acquired from SRL Pvt. Ltd. Analytical TLC was carried out on Merck silica gel G/GF 254 plates.…”

Section: ■ Conclusionmentioning

confidence: 99%

Iron(III)-Catalyzed Regioselective Synthesis of Electron-Rich Benzothiazoles from Aryl Isothiocyanates via C–H Functionalization

et al. 2023

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We report herein a direct synthetic route for the preparation of 2-arylbenzothiazoles using aryl isothiocyanates and electron-rich arenes. The synthetic route involves triflic acid promoted addition of the arenes to aryl isothiocyanates followed by FeCl3-catalyzed C–S bond formation via C–H functionalization. The approach provides the advantage of synthesis of benzothiazoles without the conventional use of aryl aldehyde/carboxylic acid precursors employing the less expensive iron(III) catalyst.

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“…However, these processes required toxic reagents, anhydrous condition. The alternative strategy is the reaction amines and carbon disulfide followed by desulfurization with various desulfurizing agents [32][33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48] as shown in Scheme 1B, path 2. Nonetheless, most of reported methods involve either using harsh conditions or toxic oxidizing agents.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Synthesis of Isothiocyanates from Amines Mediated by Carbon Tetrabromide

et al. 2023

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In this work, we successfully prepared isothiocyanates in onepot manner from the corresponding amines using carbon tetrabromide as a desulfurizing agent. The in situ formation of dithiocarbamate salts from amines followed by desulfurization using carbon disulfide provided various isothiocyanates in good to excellent yields. Moreover, our method can be extended to prepare unsymmetrical thioureas in one-pot process. Both methods are applicable to large scale synthesis. The benefits of this reaction include one-pot synthesis, mild condition, simple operation, and metal-free process.

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Iron-promoted one-pot approach: Synthesis of isothiocyanates

Cited by 13 publications

References 44 publications

Dithiocarbamate Complexes as Single Source Precursors to Nanoscale Binary, Ternary and Quaternary Metal Sulfides

Dithiocarbamate Complexes as Single Source Precursors to Nanoscale Binary, Ternary and Quaternary Metal Sulfides

Iron(III)-Catalyzed Regioselective Synthesis of Electron-Rich Benzothiazoles from Aryl Isothiocyanates via C–H Functionalization

One‐Pot Synthesis of Isothiocyanates from Amines Mediated by Carbon Tetrabromide

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