Iron‐Mediated Desulphurization Towards the Synthesis of 2‐Halo Aromatic Isothiocyanates

Pinapati, Srinivasarao; Mandapati, Usharani; Rudraraju, Ramesh Raju

doi:10.1002/slct.201601602

Cited by 17 publications

(5 citation statements)

References 55 publications

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“…Numerous methods using CS 2 have been reported to overcome these limitations. 55–75 Several methods have been explored to broaden the substrate scope of electron-deficient anilines and aminopyridines. 55,57–61,67,71,72,74,75 Moreover, employing a strong base, 69 ball milling, 56 a photoredox catalyst, 72 an electrolytic reaction, 73 or an appropriate desulfurization reagent 60,61,68,71 enables the one-step synthesis of isothiocyanates.…”

Section: Synthesis Of Isothiocyanates With Primary Amines (Type A)mentioning

confidence: 99%

“…55–75 Several methods have been explored to broaden the substrate scope of electron-deficient anilines and aminopyridines. 55,57–61,67,71,72,74,75 Moreover, employing a strong base, 69 ball milling, 56 a photoredox catalyst, 72 an electrolytic reaction, 73 or an appropriate desulfurization reagent 60,61,68,71 enables the one-step synthesis of isothiocyanates. Table 1 provides a comprehensive review of the progress in dithiocarbamate salt protocols over the past decade.…”

Section: Synthesis Of Isothiocyanates With Primary Amines (Type A)mentioning

confidence: 99%

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Recent advancement in the synthesis of isothiocyanates

Maeda,

Murakami

2024

Chem. Commun.

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Section: Synthesis Of Isothiocyanates With Primary Amines (Type A)mentioning

confidence: 99%

Section: Synthesis Of Isothiocyanates With Primary Amines (Type A)mentioning

confidence: 99%

Recent advancement in the synthesis of isothiocyanates

Maeda,

Murakami

2024

Chem. Commun.

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“…Several methods have been explored to broaden the substrate scope of electron-deficient anilines and aminopyridines. [55,[57][58][59][60][61]67,71,72,74,75] Moreover, employing a strong base [69] , ball milling [56] , a photoredox catalyst [72] , an electrolytic reaction [73] , or an appropriate desulfurylating reagent [60,61,68,71] enables the one-step synthesis of isothiocyanates.…”

Section: -2 Synthesis Of Isothiocyanates Via Dithiocarbamate Saltmentioning

confidence: 99%

Recent Advancement in Synthesis of Isothiocyanates

Maeda,

Murakami

2023

Preprint

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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, they have attracted the attention of biologists and chemists. This review summarizes recent advancements in the synthesis of isothiocyanates. Access to a variety of starting materials is important to prepare isothiocyanates with diverse structures. This review categorizes synthetic methods into three types based on the starting materials and functional groups: (i) Type A, derived from primary amines; (ii) Type B, derived from other nitrogen functional groups; and (iii) Type C, derived from non-nitrogen groups. Recent trends in synthetic methods have revealed the prevalence of type-A reactions derived from primary amines. However, Type B reactions have rarely been reported. Notably, over the past four years, there has been a notable increase in Type C reactions, indicating a growing interest in non-nitrogen-derived isothiocyanates. Overall, this review not only outlines the advancements in the synthesis of isothiocyanates but also highlights trends in the methodology.

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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‐Mediated Desulphurization Towards the Synthesis of 2‐Halo Aromatic Isothiocyanates

Cited by 17 publications

References 55 publications

Recent advancement in the synthesis of isothiocyanates

Recent advancement in the synthesis of isothiocyanates

Recent Advancement in Synthesis of Isothiocyanates

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

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