4,4′-Azopyridine as an easily prepared and recyclable oxidant for synthesis of symmetrical disulfides from thiols or alkyl halides(tosylates)/thiourea

Khalili, Dariush; Iranpoor, Nasser; Firouzabadi, Habib

doi:10.1080/17415993.2015.1070266

Cited by 11 publications

(6 citation statements)

References 99 publications

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“…There is some research dedicated to cross-coupling reactions between arylboronic acids and disulfides − or diselenides and Se (0) ,− in the presence of copper(I) and copper(II) salts. Different investigations show the possibility of diselenides formation from corresponding selenols under air conditions or in the presence of copper salts. − However, in the present work, in comparison to our earlier study which is devoted to cross-coupling reaction of sulfur-containing analogues, the diselenide 9 is not detected in the model arylation reaction according to LCMS investigation and in the blank experiment (selenohydantoin 5 { 1 , 1 } (1 equiv), copper acetate (II) monohydrate (1.1 equiv), 1,10-phenantroline (2.2 equiv) in dichloroethane). Moreover we have obtained 9 by specific oxidation of 5 { 1 , 1 } via sulfuryl chloride, but the reaction between diselenide 9 and phenylboronic acid under standard conditions does not lead to the desired product 7 { 1 , 1 , 1 }.…”

Section: Resultscontrasting

confidence: 70%

Copper-Promoted C–Se Cross-Coupling of 2-Selenohydantoins with Arylboronic Acids in an Open Flask

et al. 2019

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The modification of Chan–Lam–Evans cross-coupling reaction for the selective Se-arylation of 2-selenohydantoins under base-free mild conditions via aryl boronic acids is described herein. This approach was used to synthesize novel 5-arylidene-3-substituted-2-(arylselanyl)-imidazoline-4-ones with high yields. The anticancer activity of the final compounds was evaluated in vitro against different cancer cells, and thus, the possibility of 5-arylidene-3-substituted-2-(arylselanyl)-imidazoline-4-ones successful application as cytotoxic agents was demonstrated.

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Section: Resultscontrasting

confidence: 70%

Copper-Promoted C–Se Cross-Coupling of 2-Selenohydantoins with Arylboronic Acids in an Open Flask

et al. 2019

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“…Finally, the target product SHS was obtained by oxidation of the 6-mercapto-1-hexanesulfonic acid sodium salt with 4,4 -azopyridine. 36 SHS and SES were carefully characterized by 1 H-NMR, 13 C-NMR and mass spectrometry to ensure the correct structure. The target products SHS and SES were recrystallized from EtOH/H 2 O mixed solvents three times to reduce the residual halide ions.…”

Section: Resultsmentioning

confidence: 99%

Effects of Accelerator Alkyl Chain Length on the Microvia Filling Performance in Copper Superconformal Electroplating

Luo¹,

Li²,

Shi³

et al. 2019

J. Electrochem. Soc.

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In addition to the commercialized accelerator bis-(sodium sulfopropyl)-disulfide (SPS), we designed and synthesized two other disulfide compounds, namely, bis-(sodium sulfohexyl)-disulfide (SHS) and bis-(sodium sulfoethyl)-disulfide (SES), to investigate the effect of their alkyl chain lengths on the microvia filling performance. The galvanostatic measurements show that the addition of Cl − to different accelerator-containing solutions leads to the same synergistic effects at a current density of 20 mA/cm 2 , indicating that the interactions between accelerators and Cl − are independent of their alkyl chain lengths. However, when both Cl − and a suppressor are present, the alkyl chain length in accelerators strongly impacts their anti-suppressor strength, which increases with the growth of the alkyl chain length, reaches a maximum (SPS) and then decreases. A possible adsorption and interaction model was proposed to explain the difference of anti-suppressor effects, and microvia filling plating experiments were carried out to evaluate the effects on the filling performance. It was found that both SES and SPS, which have appropriate molecular lengths and relatively strong antagonistic effects against polyethylene glycol (PEG) and Cl − ensemble, achieved complete microvia filling. For SHS, due to the overlong alkyl chain and weak antagonistic effect against PEG and Cl − , no microvia was completely filled.

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“…不仅避免了传统使用恶臭硫醇作为硫源的弊端, 还可以同时高效构建两类含硫化合物(Scheme 10) [32] . [33] . 环状含三个硫原子化合物 79 可以用相应的对称烯基过硫化合物 78 为原料, 与硫化氢气体环化得到(Scheme 11b) [34] .…”

Section: 硫醚类unclassified

Recent Progress in the Sulfur-Containing Perfume & Flavors Construction

Wang¹,

Wang²,

Jiang³

2019

Chin. J. Org. Chem.

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Scientists have found more and more sulfur compounds in food with the development of science and technology, high-precision analytical methods and equipment. In 2015, Flavor and Extract Manufactures Association of the United State published 2816 safe flavors, and there are more than 388 sulfur-containing compounds, accounting for more than 13%. The main smell of sulfur-containing flavors is food, especially the non-staple food and dishes. It is mainly used as food flavor, flower flavor and fruity flavor. Due to the increase of sulfur-containing perfume and flavors demand, its production scale is increasing, the research on synthesis methods is also deepening, and the green and efficient construction methods are also constantly reported. In this review, the recent progress in the construction of sulfide, thiol, thioester and polysulfide perfume & flavors is summarized.

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4,4′-Azopyridine as an easily prepared and recyclable oxidant for synthesis of symmetrical disulfides from thiols or alkyl halides(tosylates)/thiourea

Cited by 11 publications

References 99 publications

Copper-Promoted C–Se Cross-Coupling of 2-Selenohydantoins with Arylboronic Acids in an Open Flask

Copper-Promoted C–Se Cross-Coupling of 2-Selenohydantoins with Arylboronic Acids in an Open Flask

Effects of Accelerator Alkyl Chain Length on the Microvia Filling Performance in Copper Superconformal Electroplating

Recent Progress in the Sulfur-Containing Perfume & Flavors Construction

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