Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water

Fu, Zhiqiang; Yuan, Wenhao; Chen, Ning; Yang, Zhanhui; Xu, Jiaxi

doi:10.1039/c8gc02261e

Cited by 43 publications

(41 citation statements)

References 113 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Most of the time, this dithiocarbamate salt is isolated prior to desulfurization. There are many available desulfurization methods; this review will focus on the use of 11 different agents, namely thiophosgene, 11 triphosgene, 13 claycop, 14 hydrogen peroxide, 15 iodine, 16 lead nitrate, 17 ethyl chloroformate, 18 cobalt(II) chloride, 19 copper(II) sulfate, 20 sodium persulfate, 5 and tosyl chloride. 21 These reagents are summarized in Table 1.…”

Section: Scheme 2 Reaction Of a Primary Amine With Thiophosgene In Thmentioning

confidence: 99%

“…Another method uses sodium persulfate 5 as the desulfurization agent. This is an especially efficient method, as it is able to obtain a wide scope of isothiocyanates, including alkyl, aryl, and amino acid derivatives.…”

Section: Scheme 8 Ethyl Chloroformate As Desulfurization Agent 18mentioning

confidence: 99%

“…This is an especially efficient method, as it is able to obtain a wide scope of isothiocyanates, including alkyl, aryl, and amino acid derivatives. 5 It is of particular importance that this method permits the synthesis of chiral isothiocyanates. 5 This is not the case when using any of the methods described above, except for thiophosgene.…”

Section: Scheme 8 Ethyl Chloroformate As Desulfurization Agent 18mentioning

confidence: 99%

“…5 It is of particular importance that this method permits the synthesis of chiral isothiocyanates. 5 This is not the case when using any of the methods described above, except for thiophosgene. This procedure has been demonstrated to work as the traditional two-step method, where the dithiocarbamate salt is isolated and then treated with the desulfurization agent, or as a one-pot method in H 2 O where the dithiocarbamate salt is generated in situ.…”

Section: Scheme 8 Ethyl Chloroformate As Desulfurization Agent 18mentioning

confidence: 99%

“…This procedure has been demonstrated to work as the traditional two-step method, where the dithiocarbamate salt is isolated and then treated with the desulfurization agent, or as a one-pot method in H 2 O where the dithiocarbamate salt is generated in situ. 5 Persulfate salts are excellent oxidative desulfurization agents, because they are stable, easy to handle, inexpensive, and green. 5 Furthermore, this methodology has also been used for large-scale work, requiring only recrystallization from ethanol to purify.…”

Section: Scheme 8 Ethyl Chloroformate As Desulfurization Agent 18mentioning

confidence: 99%

See 4 more Smart Citations

Synthesis of Isothiocyanates: An Update

Eschliman¹,

Bossmann

2019

Synthesis

View full text Add to dashboard Cite

Isothiocyanates (ICTs) are a group of molecules that can be used for many different purposes, they exhibit anticancer, antimicrobial, antibiotic, and anti-inflammatory properties. The synthesis of isothiocyanates has been a focus of many researchers for nearly the past 100 years. One of the most common synthetic methods is to form a dithiocarbamate salt, either as the first step or in situ, and then treat the salt with a desulfurization agent to reach the isothiocyanate. There are many different desulfurization agents available. Among these, there are eleven in particular that will be discussed in this short review, namely thiophosgene, lead nitrate, ethyl chloroformate, hydrogen peroxide, triphosgene, iodine, cobalt, copper, sodium persulfate, claycop, and tosyl chloride. There are four additional particular methodologies that stand out from the literature available on this topic that will be covered, namely the production of isothiocyanates from hydroximoyl chlorides, via elemental sulfur, microwave-assisted synthesis, and through the tandem Staudinger/aza-Wittig reactions.1 Introduction1.1 Metabolism of Glucosinolates2 Synthesis of Isothiocyanates2.1 Isothiocyanates from the Decomposition of Dithiocarbamate Salts2.2 Isothiocyanates from Hydroximoyl Chlorides2.3 Isothiocyanates Produced via Elemental Sulfur2.4 Microwave-Assisted Synthesis of Isothiocyanates2.5 Isothiocyanates via the Tandem Staudinger/aza-Wittig Reactions3 Conclusion

show abstract

Section: Scheme 2 Reaction Of a Primary Amine With Thiophosgene In Thmentioning

confidence: 99%

Section: Scheme 8 Ethyl Chloroformate As Desulfurization Agent 18mentioning

confidence: 99%

Section: Scheme 8 Ethyl Chloroformate As Desulfurization Agent 18mentioning

confidence: 99%

Section: Scheme 8 Ethyl Chloroformate As Desulfurization Agent 18mentioning

confidence: 99%

Section: Scheme 8 Ethyl Chloroformate As Desulfurization Agent 18mentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of Isothiocyanates: An Update

Eschliman¹,

Bossmann

2019

Synthesis

View full text Add to dashboard Cite

show abstract

Iron‐Promoted Redox Access to 2‐Aminobenzoxazoles from Amines, Carbon Disulfide and 2‐Nitrophenols

Long Le,

Yen Tran,

Anh Nguyen

et al. 2024

Asian J Org Chem

View full text Add to dashboard Cite

A method to assemble 2‐aminobenzoxazoles via iron‐catalyzed redox condensation of amines, carbon disulfide and 2‐nitrophenols is reported. The reaction features advantages of environmentally friendly iron catalyzed conditions, readily available starting materials, and excellent atom‐, step‐ and redox economy compared to known protocols. Experimental investigation suggests a mechanism encompassing iron‐catalyzed reduction of the nitro group of 2‐nitrophenols by the dithiocarbamate group from amine‐CS2 adduct.

show abstract

Visible‐Light‐Induced Metal‐Free Synthesis of 2‐Phosphorylated Thioflavones in Water

et al. 2019

View full text Add to dashboard Cite

The introductiono fp hosphorus functional groups into the skeleton of thioflavonesi sa na ttractive task and of great significance. Herein, am etal-free visible-light-induced radicalc ascade cyclization was developed for the preparation of 2-phosphorylated thioflavones from methylthiolated alkynones and phosphine oxides. In water as ag reen reaction medium, a large number of such 2-phosphorylated thioflavones were prepared, catalyzed by 4CzIPN [1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene] under visible-light irradiation.T hese reactions could be performed ata mbient temperature and feature simple operation, wide reactions cope, and recyclability of aqueous media.

show abstract

Na₂S₂O₈-mediated efficient synthesis of isothiocyanates from primary amines in water

Abstract: Two procedures to synthesize isothiocyanates from primary amines are developed, with water as a solvent and sodium persulfate as an oxidant.

Cited by 43 publications

References 113 publications

Synthesis of Isothiocyanates: An Update

Synthesis of Isothiocyanates: An Update

Iron‐Promoted Redox Access to 2‐Aminobenzoxazoles from Amines, Carbon Disulfide and 2‐Nitrophenols

Visible‐Light‐Induced Metal‐Free Synthesis of 2‐Phosphorylated Thioflavones in Water

Contact Info

Product

Resources

About