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1.
Org Lett ; 2024 Sep 18.
Artículo en Inglés | MEDLINE | ID: mdl-39291854

RESUMEN

Herein, we reported a copper(0)-catalyzed reductive coupling of disulfurating reagents and (hetero)aryl/alkyl halides. Copper(0) can be directly inserted into tetrasulfide and then undergoes reductive coupling with (hetero)aryl Iodides to construct disulfide. The method features the unprecedented use of copper(0)-catalyzed disulfurating reagents (tetrasulfides) in cross-coupling chemistry and is convenient with broad substrate scopes, even applicable to different halogenated hydrocarbons. It is worth noting that the methodology is practical with the late-stage modification of bioactive scaffolds of pharmaceuticals. In the meantime, the synthesis of disulfides is successfully achieved on a gram scale, indicating the approach is highly valuable.

2.
J Org Chem ; 89(18): 13386-13400, 2024 Sep 20.
Artículo en Inglés | MEDLINE | ID: mdl-39258469

RESUMEN

A tandem cyclization reaction of enynones with tetrasulfides has been developed under manganese-promoted conditions, leading to the high-yield formation of various furanmethyl disulfides. This reaction is characterized by readily available starting materials, mild reaction conditions, and a broad substrate scope, making it attractive and practical. It provides a new strategy for the synthesis of disulfide-containing functionalized furans.

3.
Int J Biol Macromol ; 280(Pt 3): 136015, 2024 Sep 24.
Artículo en Inglés | MEDLINE | ID: mdl-39326596

RESUMEN

Dialdehyde-soluble starch (DAS) and polyethyleneimine (PEI) were used to coat the polyvinylidene fluoride (PVDF) membrane for improving its antifouling and multifunctional properties through a combination of dip-coating and spray-coating techniques. The resulting membrane demonstrated excellent hydrophilicity and underwater oleophobicity due to hydrophilic DAS and PEI on its surface. The membrane achieved an impressive oil removal rate of 99.8 % and a flux 1420.8 ± 26.5 L·m-2·h-1 when it was used for oil-water emulsion separation. The hydration layer formed by the DAS and PEI greatly enhanced the membrane antifouling property, and its flux recovery rate was up to 96.6 % in BSA filtration experiments. The positive charge PEI and the negative charge DAS contributed to high separation efficiency of 99.1 % for the anion dye MO with the membrane D10P20, and high separation efficiency of 88.3 % for the cation dye RhB with the membrane P5D20. In addition, the coating layer was stable due to the cross-linked DAS and PEI. This research contributes greatly to the preparation of antifouling and multifunctional membrane using environmentally friendly material including polysaccharide derivatives and water soluble polymer.

4.
J Org Chem ; 89(12): 8804-8814, 2024 Jun 21.
Artículo en Inglés | MEDLINE | ID: mdl-38860924

RESUMEN

1,4-/1,3-Regioselective bifunctionalization of 1,3-enynes with selenosulfonates in water under catalyst-free conditions for the construction of sulfonyl allene and 1,3-disulfonyl-conjugated dienes respectively have been developed. The reactions feature mild reaction conditions in aqueous solution and remarkable regioselectivity controlled by substrates.

5.
J Hazard Mater ; 471: 134341, 2024 Jun 05.
Artículo en Inglés | MEDLINE | ID: mdl-38642496

RESUMEN

Developing high-efficiency membrane for oil and dye removal is very urgent, because wastewater containing them can cause great damage to human and environment. In this study, a coated membrane was fabricated by applying DAC and PEI onto the commercial PVDF microfiltration membrane for supplying the demand. The coated membrane presents superhydrophlic and superoleophobic properties with a water contact angle of 0o and underwater oil contact angle exceed 150°, as well as excellent low underwater oil adhesion performance. The coated membrane shows high separation efficiency exceeded 99.0% and flux 350.0 L·m-2·h-1 when used for separating for six kinds of oil including pump oil, sunflower oil, n-hexadecane, soybean oil, diesel and kerosene in water emulsions. Additionally, the coated membrane can effectively remove anionic dyes, achieving rejection rates of 94.7%, 93.4%, 92.3%, 90.7% for the CR, MB, RB5, AR66, respectively. More importantly, the membrane was able to simultaneously remove emulsified oil and soluble anionic dyes in wastewater containing both of them. Therefore, this novel coated membrane can be a promising candidate for treating complex wastewater.

6.
Org Lett ; 26(17): 3634-3639, 2024 May 03.
Artículo en Inglés | MEDLINE | ID: mdl-38660998

RESUMEN

In this paper, we report an unprecedented copper-catalyzed disulfides or sulfides coupling reaction involving unactivated alkyl halides and N-dithiophthalimides. This reaction can be conducted under mild conditions using low-cost metal catalysts and exhibits high chemical selectivity and functional group compatibility, enabling the efficient assembly of various sulfides and disulfides.

7.
Chem Asian J ; 19(11): e202400086, 2024 Jun 03.
Artículo en Inglés | MEDLINE | ID: mdl-38676953

RESUMEN

A visible light-catalyzed radical coupling reaction of polysulfide reagents with aryldiazonium was developed, which gave thiosulfonates under mild conditions. In this reaction, the thiosulfonates were isolated in good yields with a broad tolerance to functional groups. And the synthesis of diaryl monosulfides were achieved through a step-by-step reaction of two molecular aryldiazonium with DBSPS, where the sulfur source was provided by DBSPS. It was worth noting that the reaction of this monosulfides could also be achieved by a one pot two-step process. The described polysulfide reagents were able to produce three new radicals: sulfonyl radicals, sulfur-sulfonyl radicals and sulfur-sulfur-sulfonyl radicals.

8.
J Org Chem ; 89(1): 363-372, 2024 Jan 05.
Artículo en Inglés | MEDLINE | ID: mdl-38085815

RESUMEN

Herein, we have developed a new method for the synthesis of ((methyl-d3)sulfonyl)ethyne, which is cost-effective and environmentally friendly and can be synthesized at the gram level. As an ideal thiol-yne reagent, it can be reacted with various types of thiols to afford (Z)- and (E)-type vinyl sulfides under different conditions with high selectivity. In addition, it can complete the conformational transition from Z- to E-type products under suitable conditions, and can also carry out further derivatization smoothly. The deuterium content of all products was greater than 99%. The preliminary mechanistic studies support the visible light-mediated radical course, and herein provide a novel and efficient synthetic strategy for the direct introduction of deuterated methyl groups, enriching the methods for the construction of C-S bond-containing compounds.

9.
Org Lett ; 25(51): 9207-9212, 2023 Dec 29.
Artículo en Inglés | MEDLINE | ID: mdl-38113225

RESUMEN

Sulfone compounds and thioether compounds are two highly valuable classes of compounds, but it is challenging to prepare sulfone and thioether compounds simultaneously and efficiently. Here we report that sulfides/selenides and sulfones can be obtained simultaneously using allyl bromide/benzyl bromide-activated alkyl bromides and thiosulfonates/selenosulfonates using a nickel-catalyzed reductive coupling and SN2 synergistic strategy, which is characterized by excellent atom and step economy, mild reaction conditions, broad functional group compatibility, and excellent yields.

10.
J Org Chem ; 88(22): 15871-15880, 2023 Nov 17.
Artículo en Inglés | MEDLINE | ID: mdl-37882877

RESUMEN

Herein, we report a novel method for the synthesis of thioesters and acyl disulfides via nickel-catalyzed reductive cross-electrophile coupling of acid chlorides with tetrasulfides. This approach for the synthesis of thioesters and acyl disulfides is convenient and practical under mild reaction conditions, relying on easy availability. In addition, a wide range of thioesters and acyl disulfides were obtained in medium to good yields with good functional group tolerance. Moreover, thioesters and acyl disulfides can also be prepared at the gram scale, indicating that they have certain potential for industrial application.

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