Micelle-enabled Bromination of α-Oxo Ketene Dithioacetals: Mild and Scalable Approach via Enzymatic Catalysis DOI
Thao Nguyen Thanh Huynh, Khuyen Thu Nguyen,

Chisanu Krongyut

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

The bromination of α-oxo ketene dithioacetals using KBr/H2O2, catalyzed by Curvularia inaequalis vanadium chloroperoxidase (CiVCPO), has been successfully demonstrated. A comparative study enzymatic processes "on water" versus "in water", 2 wt% the surfactant TPGS-750-M revealed that in-water protocol not only provides higher yields but also accommodates a broader substrate scope. This method in an aqueous micellar medium enabled preparation brominated fair to excellent (23 examples). In system, concentration was increased up 50 mM, and amounts brominating agents KBr H2O2 were reduced approximately 2.0 equivalents without compromising efficiency. Notably, this process allows for gram-scale high yields. Key advantages include its benign eco-friendly nature, use water as green solvent, potential large-scale production dithioacetals.

Language: Английский

Sustainable Synthesis of α-Glucosidase Inhibitors by Gas-Free Pd-Carbonylation of Nature-Based Hydroxytyrosol DOI Open Access
Francesco Messa,

Domenico Armenise,

Anselma Liturri

et al.

Catalysts, Journal Year: 2025, Volume and Issue: 15(3), P. 202 - 202

Published: Feb. 21, 2025

This study outlines the sustainable synthesis of novel hydroxytyrosol (HT) and tyrosol (T) ester derivatives via a Pd-catalyzed alkoxycarbonylation aromatic iodides. The high sustainability process is attributed to use (1) solid carbon monoxide source, Mo(CO)6, in place dangerous gaseous CO; (2) biomass-derived organic solvent, CPME (cyclopentyl methyl ether); (3) naturally occurring hydroxylated compounds, such as HT T, which could be derived from agricultural waste rather than produced petroleum-based sources. method enables regioselective preparation various T esters short reaction time (4–8 h), under mild temperatures (80 °C), with moderate-to-excellent yields (62–93%). Moreover, vitro biological tests have demonstrated that, addition well-known antioxidant properties typical natural phenolic compounds some newly synthesized safe profile are effective inhibitors α-glucosidase potential application management hyperglycemia. synthetic approach offers promising strategy for exploring biologically relevant chemical space, bridging gap between products drug synthesis.

Language: Английский

Citations

0

Micelle-Enabled In Situ Surface Modification of Porous Organic Polymers: Formation of Heterogeneous Microcolony for Efficient Suzuki–Miyaura Coupling in Water DOI

Rajan Yadav,

Pritesh Keshari,

Susanta Hazra

et al.

ACS Applied Materials & Interfaces, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

Synthesis of water-stable and dispersible heterogeneous catalysts having high catalytic efficiency is more challenging compared with homogeneous due to their low dispersity, activity, spatial confinement active centers in bulk water. Herein, we are describing systematic studies for the development microconfinement participation aqueous micelles via temporal surface modification porous organic polymer derived from phosphine ligands. Detailed investigations using various techniques such as transmission electron microscopy (TEM), scanning (SEM), tensiometry, confocal laser (CLSM), fluorescence lifetime imaging (FLIM) have been used understand role micelles, reagents, materials generation microcolonies Two-color crossover experiments also performed exchange reagents or vice versa, materials. The surfactant-modified ligation stabilization palladium, which was evidenced by high-resolution (HR-TEM), high-angle annular dark-field (HAADF-STEM), X-ray photoelectron spectroscopy (XPS) analysis. act confined space catalysis water showcasing Suzuki-Miyaura cross-coupling reaction a ppm level Pd loading under mild conditions. catalyst found be recyclable five cycles; easy scale-up C-C couplings additional features. Moreover, these data provide an opportunity revising models micellar systems that underpin sustainable

Language: Английский

Citations

0

Oxidation of l-tyrosine by diperiodatocuprate(III) in CPC micellar medium, facilitated by Ru(III) DOI
Abhishek Srivastava, Neetu Srivastava, Vinay K. Singh

et al.

Tenside Surfactants Detergents, Journal Year: 2025, Volume and Issue: unknown

Published: April 8, 2025

Abstract The oxidation of amino acids is interesting due to the different molecules generated by oxidants. This research crucial understand role in redox processes and identify active species Ru(III) diperiodatocuprate(III) (DPC). purpose present analyze effect cationic surfactant on catalysed l -tyrosine ( -Tyr) DPC. progression reaction was evaluated using pseudo-first-order scenario as a metric for [OH − ], [DPC], ionic strength, [ -Tyr], [Ru(III)], [IO 4 [surfactant], temperature. Over range concentrations studied, observed exhibits kinetic order less than one with respect both ] negative fractional first-order dependence [Ru(III)] [DPC]. constancy rate electrolyte addition suggests zero salt effect. markedly increased solution acting catalyst at ppm concentration. micellar media cetylpyridinium chloride (CPC) significantly accelerates desired reaction, achieving fourfold increase. compatibility CPC -Tyr DPC particularly noteworthy.

Language: Английский

Citations

0

Palladium Complex Grafted on PEG-Based Amphiphilic Polymers as ppm Level Micellar Catalysts for Suzuki–Miyaura Coupling in Water DOI
Song Xiao,

Minghang Wang,

Yiming Liu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

A series of bisphosphine-grafted amphiphilic polymers based on polyethylene glycol-poly(vinylethylene glycol) (PEG-PVEG) copolymers have been synthesized by using allylic etherification polymerization as a pivotal step. Self-assembling the palladium complexes obtained into spherical micelles has investigated UV-vis, DLS and TEM analysis. The outstanding catalytic performance present micellar catalyst evidenced in aqueous Suzuki-Miyaura coupling reaction, achieving remarkable efficiency even at low loading 100 ppm within 2 h.

Language: Английский

Citations

0

Sustainable and Scalable Amidations in Water Using Continuous Slurry-Flow Technology DOI Creative Commons

Saravanan Rajendran,

Sabrina Kogler,

Philipp Kögl

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Language: Английский

Citations

0

Recent advances on carbon nitride-based photocatalysts for organic transformations in aqueous media DOI
Pengfei Zhou, Yunfei Cai, Yurong Tang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(16), P. 4624 - 4638

Published: Jan. 1, 2024

This review highlights recent advancements in photocatalytic organic transformations aqueous media employing the water-compatible solid-state sensitizer carbon nitride and its derivatives as catalysts.

Language: Английский

Citations

3

Micelles Enabled Nickel-Catalyzed P-Arylation of Aromatic Phosphine Oxide in Water Under Mild Conditions DOI

Pritesh Keshari,

Rajan Yadav,

Priya Mata

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 12(31), P. 11473 - 11479

Published: July 15, 2024

A nonionic surfactant has been developed from agricultural waste and its potential application for the Ni-catalyzed C–P cross-coupling reaction in water. The was fully characterized by various spectroscopic imaging techniques. size of micelles morphological changes presence catalysts/substrates were established using transmission electron microscopy (TEM), dynamic light scattering (DLS), confocal microscopy. Controlled 31P NMR, 19F mass spectrometry, X-ray photoelectron spectroscopy (XPS) analysis revealed possible reactive intermediates mechanisms. synthesis shown 20 g 1 scale, respectively.

Language: Английский

Citations

3

Photochemical cyclopropanation in aqueous micellar media – experimental and theoretical studies DOI Creative Commons
Joseph P. Milton, Adam Milanowski, Martin Andersson

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(33), P. 4483 - 4486

Published: Jan. 1, 2024

While in nature, reactions occur water-based confined compartments, for a long time, water has been often regarded as an unsuitable medium organic reactions. We have, however, found that photochemical cyclopropanation of styrenes with diazo compounds or their precursors can be performed micellar systems. COSMO-RS studies revealed the reactivity correlates predicted critical micelle concentration (CMC), higher CMC values delivering yields.

Language: Английский

Citations

2

The ligand: an overlooked element in sustainable catalysis DOI
Sachin Handa

Trends in Chemistry, Journal Year: 2024, Volume and Issue: 6(8), P. 428 - 431

Published: June 20, 2024

Language: Английский

Citations

2

Aqueous Micellar Environment Impacts the Co-Catalyzed Phototransformation: A Case Study DOI Creative Commons
Aleksandra Wincenciuk, Piotr Cmoch, Maciej Giedyk

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(29), P. 19828 - 19838

Published: July 9, 2024

In recent years, methodologies that rely on water as the reaction medium have gained considerable attention. The unique properties of micellar solutions were shown to improve regio-, stereo-, and chemoselectivity different transformations. Herein, we demonstrate aqueous environment is a suitable for visible light driven cobalt-catalyzed involving radical species. this system, reduced vitamin B

Language: Английский

Citations

2