Hyperbranched Polymer Immobilized Palladium Nanoparticles as an Efficient and Reusable Catalyst for Cyanation of Aryl Halides and Reduction of Nitroarenes DOI
Mohammad Gholinejad,

Mohammad Shojafar,

José M. Sansano

и другие.

SSRN Electronic Journal, Год журнала: 2022, Номер unknown

Опубликована: Янв. 1, 2022

A new nitrogen-rich hyperbranched polymer comprising imidazolium and triazole moieties used for stabilization of Pd nanoparticles. The resulting material, PolyTZ-IL@Pd NPs, was characterized with different techniques including Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), photoelectron (XPS), energy dispersive X-Ray (EDX), transmission electron microscopy (TEM) analysis. NPs has been as an efficient catalyst in the reduction nitroarenes to amines cyanation aryl bromides iodides. showed high stability recyclability recycled at least 10 times 1-chloro-4-nitrobenzene 5 iodobenzene.

Язык: Английский

Efficient Recycling of Catalyst‐Solvent Couples from Lewis Acid‐Catalyzed Asymmetric Reactions in Water DOI
Taku Kitanosono,

Fangqiu Lu,

K. Masuda

и другие.

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(25)

Опубликована: Март 31, 2022

Abstract Bioinspired supramolecular architectures were used to compartmentalize highly charged aqua scandium ions into chiral hydrophobic scaffolds for Lewis acid‐catalyzed asymmetric reactions. Recycling without significant loss in catalytic performance is a formidable task, especially This because basic impurities derived from starting materials, products, and water are competitive ligands both substrate binding metal complexation, thus poisoning the acids leading their leaching. Even when aniline used, architecture allowed effective suppression of Sc 3+ leaching reuse solvent‐catalyst couples ring‐opening reactions deactivation. Application thia‐Michael addition hydroxymethylation was also demonstrated. The successful recycling environments underpins exceptionally high robustness acid catalyst.

Язык: Английский

Процитировано

14

Cascade Processes with Micellar Reaction Media: Recent Advances and Future Directions DOI Creative Commons
Christina Tang, Bridget T. McInnes

Molecules, Год журнала: 2022, Номер 27(17), С. 5611 - 5611

Опубликована: Авг. 31, 2022

Reducing the use of solvents is an important aim green chemistry. Using micelles self-assembled from amphiphilic molecules dispersed in water (considered a solvent) has facilitated reactions organic compounds. When performing micelles, hydrophobic effect can considerably accelerate apparent reaction rates, as well enhance selectivity. Here, we review micellar media and their potential role sustainable chemical production. The focus this applications engineered systems for (surface-active ionic liquids, designer surfactants, block copolymers) media. Micelles are versatile platform large array chemistries using bulk solvent. Building on foundation, synthetic sequences combining several steps one pot have been developed. Telescoping multiple reduce solvent waste by limiting volume solvents, eliminating purification processes. Thus, particular, recent advances "one-pot" multistep achieved with medicinal chemistry agrochemistry. Photocatalyzed also discussed. In addition to emphasize process (steps isolate product reuse catalyst).

Язык: Английский

Процитировано

13

Palladium-Catalyzed Direct Decarbonylative Cyanation of Aryl Carboxylic Acids DOI
Guofu Zhang,

Huihui Miao,

Chenfei Guan

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(19), С. 12791 - 12798

Опубликована: Сен. 12, 2022

The direct transformation of aryl carboxylic acids to nitrile compounds is an interesting topic because are not only abundant in nature but also inexpensive and stable. Here, the synthesis a series nitriles by palladium-catalyzed decarbonylative cyanation without base has been achieved. successful drug molecules Gram-scale reaction verify practicality operability this method analyzed.

Язык: Английский

Процитировано

13

Hyperbranched polymer immobilized palladium nanoparticles as an efficient and reusable catalyst for cyanation of aryl halides and reduction of nitroarenes DOI
Mohammad Gholinejad,

Mohammad Shojafar,

José M. Sansano

и другие.

Journal of Organometallic Chemistry, Год журнала: 2022, Номер 970-971, С. 122359 - 122359

Опубликована: Апрель 25, 2022

Язык: Английский

Процитировано

11

Pd-Catalyzed Carbonylations of Aryl/Heteroaryl Halides in Aqueous Micellar Media DOI Creative Commons
Juan C. Caravez, Madison J. Wong,

Rahul D. Kavthe

и другие.

ACS Catalysis, Год журнала: 2023, Номер 13(18), С. 12383 - 12390

Опубликована: Сен. 6, 2023

Formation of amides, acids, and thioesters are readily fashioned from precursor aryl/heteroaryl halides under micellar catalysis conditions using W(CO)6 as a source carbon monoxide. Loadings ligated palladium catalysts usually in the 0.5 mol % range. Yields with iodides tended to be higher than those bromides. Applications targets pharmaceutical industry demonstrated, cases Merck Informer Library. Both E Factor calculations options for recycling aqueous reaction medium presented.

Язык: Английский

Процитировано

6

Effect of sustainable and confined media on the photoinduced [6π]‐electrocyclization reaction of diphenyl and N‐methyldiphenylamines DOI
María L. Salum, Stefano Protti,

Mariella Mella

и другие.

ChemPhotoChem, Год журнала: 2024, Номер unknown

Опубликована: Май 22, 2024

Abstract A systematic investigation of the photoinduced [6π]‐electrocyclization reaction diphenylamine and N‐methyldiphenylamine has been carried out under steady‐state time‐resolved conditions in homogeneous (cyclohexane, acetonitrile methanol) micellar solutions (sodium dodecyl sulfate ‐SDS, cetyltrimethylammonium chloride‐CTAC polyethylene glycol monododecyl ether‐Brij P35). The photolysis such compounds both micro‐heterogeneous media afforded corresponding carbazoles almost quantitative yield oxidative conditions. Furthermore, relative rate formation photoproducts increases when moving from to solution, due environmental confined hydrophobic core as highlighted by 1D 2D NMR (NOESY DOSY) spectroscopic analyses.

Язык: Английский

Процитировано

2

Water‐Mediated C−H Cyanation of Quinoxalin‐2(1H)‐ones and Quinoxalines Under Visible‐Light Conditions DOI
Gaurav Badhani, Subbarayappa Adimurthy

ChemistrySelect, Год журнала: 2023, Номер 8(27)

Опубликована: Июль 19, 2023

Abstract Regioselective cyanation of quinoxalin‐2(1 H )‐ones and quinoxalines with acetone cyanohydrin under aqueous aerobic visible‐light conditions at room temperature is described. Acetone utilized as a safe source for cyanation. In both cases, good functional group tolerance was observed very to quantitative yields products metal/base/ligand‐free conditions. Several control experiments revealed that, water oxygen from air are crucial the efficiency present transformation. These reactions proceed through radical pathway confirmed by scavengers. To validate feasibility process commercial syntheses, three were synthesized gram scale optimized The conversion cyanated into corresponding amides acid also performed pure obtained without column chromatographic separation.

Язык: Английский

Процитировано

5

Catalysis and inhibition of ester hydrolysis by encapsulation in micelles derived from designer surfactant TPGS-750-M DOI
Courtney J. Hastings,

Matthew S. DiNola,

Eleftheria Petratos

и другие.

Tetrahedron, Год журнала: 2023, Номер 133, С. 133271 - 133271

Опубликована: Янв. 19, 2023

Язык: Английский

Процитировано

4

The Photoinduced Electrocyclization Reaction of Triphenylamine (TPA) in Sustainable and Confined Micellar Solutions: A Steady‐State and Laser Flash Photolysis Approach DOI

Rocío A. Sanmartín,

María L. Salum, Stefano Protti

и другие.

ChemPhotoChem, Год журнала: 2021, Номер 6(4)

Опубликована: Ноя. 18, 2021

Abstract The irradiation of triphenylamine (TPA) under homogeneous (cyclohexane, acetonitrile and methanol) micellar [sodium dodecyl sulfate (SDS), cetyltrimethylammonium chloride (CTAC) polyethylene glycol monododecyl ether (Brij‐P35)] conditions has been investigated through a combined steady‐state time‐resolved spectroscopic approach. Photolysis TPA at 254 nm in different media afforded N ‐phenylcarbazole (N−PhCA) as the main photoproduct, when photoreaction was carried out solution relative rate formation N−PhCA found to be faster than due environmental confined hydrophobic core. On other hand, transient ‐phenyl‐ 4a,4b ‐dihydrocarbazole (DHC 0 ) detected fully characterized via laser flash photolysis. Finally, location within core micelle by 1D 2D NMR analyses.

Язык: Английский

Процитировано

9

Recent Advances in Organic Reactions Using Water as Solvent DOI
Chang‐Sheng Wang, Qiao Sun,

Guowei Wang

и другие.

Опубликована: Март 8, 2024

In the past two decades, water has gradually become a green and sustainable alternative to traditional organic solvents which are generally hazardous waste productive. Due its safe, nontoxic, nonflammable, cost-effective, abundant nature, been increasingly used in various types of reactions ranging from conventional oxidation, reduction, addition, substitution, condensation, cyclization classical cross-coupling, CH activation more recent photoredox, electrochemical chemoenzymatic reactions. This chapter summarizes (2017-2022) representative examples using as solvent covers related reaction mechanisms roles that plays certain Micellar-enabled aqueous facilitated by surfactants will also be discussed.

Язык: Английский

Процитировано

1