Recent advancement in the synthesis of isothiocyanates

Chemical Communications, Год журнала: 2024, Номер 60(21), С. 2839 - 2864

Опубликована: Янв. 1, 2024

Isothiocyanates exhibit various biological characteristics, including antimicrobial, anti-inflammatory, and anticancer properties. Their significance extends to synthetic chemistry, where they serve as valuable platforms for versatile transformations. Consequently, have attracted the attention of biologists chemists. This review summarizes recent advancements in synthesis isothiocyanates. Access a variety starting materials is important prepare isothiocyanates with diverse structures. categorizes methods into three types based on functional groups: (i) type A, derived from primary amines; (ii) B, other nitrogen groups; (iii) C, non-nitrogen groups. Recent trends revealed prevalence type-A reactions amines. However, B rarely been reported. Notably, over past four years, there has notable increase C reactions, indicating growing interest non-nitrogen-derived Overall, this not only outlines but also highlights methodology.

Язык: Английский

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Electrochemical Allylic C(sp³)–H Isothiocyanation via [3,3]-Sigmatropic Rearrangement

Organic Letters, Год журнала: 2024, Номер 26(21), С. 4554 - 4559

Опубликована: Май 20, 2024

The direct allylic C(sp3)–H functionalization provides a straightforward protocol for the synthesis of valuable molecules. We report herein first chemo- and site-selective method isothiocyanation various internal alkenes under mild electrochemical conditions. This exhibits broad functional group tolerance excellent selectivity can be applied late-stage bioactive Combined experimental computational studies indicate that reaction proceeds via an unexpected [3,3]-sigmatropic rearrangement.

Язык: Английский

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Isothiocyanates: happy-go-lucky reagents in organic synthesis

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(19), С. 3772 - 3798

Опубликована: Янв. 1, 2024

This review summarises the reactivity and synthetic procedures of aryl acyl isothiocyanates, a versatile reagent with multiple reactive centres.

Язык: Английский

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Bis(dialkylaminethiocarbonyl)disulfides Act as Electron Acceptors for EDA Complexes for the Synthesis of Dithiocarbamate Derivatives under Visible Light

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 14, 2025

This study proposes a green and efficient atom- step-economical method for converting hazardous CS2 to dithiocarbamate derivatives under visible light irradiation catalyst-free conditions. By the construction of novel C-S C-N bonds, series β-dicarbonyl compounds amines are incorporated into products. Under light, amine first form bis(dialkylaminethiocarbonyl)disulfides, which then react with K2CO3-activated electron donor-acceptor (EDA) complexes subsequently generate target confirms time that bis(dialkylaminethiocarbonyl)disulfides can act as acceptors an EDA complex compounds, coupled product light.

Язык: Английский

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Transition-Metal-Free Radical Approach for the Synthesis of Isothiocyanates by Pyridinium 1,4-Zwitterionic Thiolates as a Sulfur Source

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 28, 2025

Herein, we disclose a novel, mild, transition-metal-free approach to synthesizing diversely functionalized isothiocyanates from the corresponding isocyanide precursors, achieving high excellent yields (up 97%). The current method sheds light on reactivity of pyridinium 1,4-zwitterionic thiolates as an unprecedented sulfur source strikingly distinct their previously known in ionic annulation reactions, showcasing innovative organic synthesis.

Язык: Английский

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Mechanoredox-Enabled Isothiocyanation of Primary Amines Using Piezoelectric Material as the Redox Catalyst

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 7, 2025

A novel mechanoredox-enabled synthesis of aromatic and aliphatic isothiocyanates from primary amines carbon disulfide under ball milling conditions using a piezoelectric material (BaTiO3) as the redox catalyst has been developed. This method displays several features, such short reaction time, operational simplicity, room temperature air conditions, minimal solvent, broad substrate scope, recyclable cheap catalyst. Preliminary mechanistic studies revealed that highly polarized acted single-electron transfer (SET) oxidation reagent for key desulfurization process.

Язык: Английский

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Electro-Oxidative Three-Component Synthesis of 3,5-Disubstituted-1,2,4-Thiadiazoles from Amines, Amidines, and CS₂

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 29, 2025

1,2,4-Thiadiazoles, a significant class of heterocyclic compounds, are widely found in biologically active molecules. Herein, we report green electrochemical three-component reaction amines, amidines, and CS2 for the effective synthesis 3,5-disubstituted-1,2,4-thiadiazoles under metal- oxidant-free conditions. Both aliphatic aryl amines well-tolerated at room temperature simple undivided cell. A series 1,2,4-thiadiazoles prepared with excellent functional groups.

Язык: Английский

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Metal‐Free Synthesis of 2‐Aminobenzothiazoles via I₂‐Catalyzed Tandem Cyclization Reaction of Amines and Carbon Disulfide

Chinese Journal of Chemistry, Год журнала: 2023, Номер 42(8), С. 846 - 852

Опубликована: Дек. 20, 2023

Comprehensive Summary A convenient approach for the construction of 2‐aminobenzothiazoles via I 2 ‐catalyzed tandem cyclization reaction amines and carbon disulfide has been developed. The present starts from simple readily available starting materials, affording a series in up to 89% yields under metal‐free conditions. In this work, C—H/N—H functionalization was achieved multiple C‐hetero bonds were successfully constructed one pot.

Язык: Английский

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