Chemistry of “In‐Water” Reactions: Spotlights on Micellar and Phase‐Transfer Catalysis DOI
Tharique N. Ansari, Gaganpreet Kaur, Thomas J. Colacot

и другие.

Опубликована: Ноя. 8, 2024

Custom-designed additives play a crucial role in achieving desired transformations under aqueous conditions modern organic synthesis. In micellar catalysis, designer amphiphilic molecules create dynamic supramolecular structures that can dissolve reactants and catalysts conditions. This enables the to occur mild without need for hazardous solvents. Additionally, such as tetra -butyl ammonium chloride or bromides facilitate reactions through efficient transfer of reactive species between non-miscible biphasic systems. method, known phase-transfer has been instrumental challenging asymmetric chapter overviews recent advancements these respective fields, outlining fundamental principles underlying their operational mechanisms.

Язык: Английский

Aqueous Micelles as Solvent, Ligand, and Reaction Promoter in Catalysis DOI Creative Commons

Jagdeep K. Virdi,

Ashish Dusunge,

Sachin Handa

и другие.

JACS Au, Год журнала: 2024, Номер 4(2), С. 301 - 317

Опубликована: Янв. 16, 2024

Water is considered to be the most sustainable and safest solvent. Micellar catalysis a significant contributor chemistry in water. It promotes pathways involving water-sensitive intermediates transient catalytic species under micelles' shielding effect while also replacing costly ligands dipolar-aprotic solvents. However, there lack of critical information about micellar catalysis. This includes why it works better than traditional organic solvents, specific rules differ from those conventional catalysis, how limitations can addressed future. Perspective aims highlight current gaps our understanding provide an analysis designer surfactants' origin essential components. will fundamental including aqueous micelles simultaneously perform multiple functions such as solvent, ligand, reaction promoter.

Язык: Английский

Процитировано

29

Recent Highlights in Micellar Catalysis: An Industrial Outlook DOI
Tharique N. Ansari, Guolin Xu, Andrew Z. Preston

и другие.

Organic Process Research & Development, Год журнала: 2024, Номер 28(4), С. 816 - 830

Опубликована: Март 14, 2024

From the context of sustainability, contemporary synthetic organic chemistry practices require significant transformation, as indicated by various sustainability matrices like atom economy, process mass intensity (PMI), E-factor, and DOZN. These factors have evidently unveiled inherent inefficiencies intrinsic to conventional protocols identified solvents principal causative agent. In response, utilization water a primary reaction medium for transformations has emerged an appealing alternative. This approach flourished with emergence micellar catalysis, where amphiphilic molecules alter bulk aqueous medium's solvation properties promote desired chemical transformation under milder sustainable conditions. After 2010, this technology gained considerable momentum established foundational framework performing reactions conditions, consequently mitigating dependency on hazardous solvents. perspective, recent advances in field catalysis will be discussed industrial applications, along future directions challenges associated regime.

Язык: Английский

Процитировано

11

Decoupling of the Confused Complex in Oxidation of 3,3′,5,5′-Tetramethylbenzidine for the Reliable Chromogenic Bioassay DOI

Caixia Zhu,

Hong Yang, Xuwen Cao

и другие.

Analytical Chemistry, Год журнала: 2023, Номер 95(44), С. 16407 - 16417

Опубликована: Окт. 26, 2023

Regulation of the reaction pathways is a perennial theme in field chemistry. As typical chromogenic substrate, 3,3′,5,5′-tetramethylbenzidine (TMB) generally undertakes one-electron oxidation, but product (TMBox1) essentially confused complex and unstable, which significantly hampers clinic bioassays for more than 50 years. Herein, we report that sodium dodecyl sulfate (SDS)-based micelles could drive direct two-electron oxidation TMB to final stable TMBox2. Rather activation H2O2 oxidant by common natural peroxidase, substrate SDS decoupled thermodynamically favorable between TMBox2 with unreacted TMB, leading an unusual pathway. Mechanism studies demonstrated complementary spatial electrostatic isolation effects, caused confined hydrophobic cavities negatively charged outer surfaces micelles, were crucial. Further cascading glucose oxidase, as proof-of-concept application, allowed be reliably measured, even broader range concentrations without any conventional strong acid termination.

Язык: Английский

Процитировано

17

Implementation of micelle-enabled C(sp2)–C(sp3) cross-electrophile coupling in pharmaceutical synthesis DOI
Bin Wu, Ning Ye, Kangming Zhao

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(17), С. 2349 - 2352

Опубликована: Янв. 1, 2024

A sustainable C(sp 2 )–C(sp 3 ) cross-electrophile coupling was developed between readily available 5-bromophthalide and 1-benzyl-4-iodopiperidine under micellar conditions, leading to a key intermediate of one our development compounds.

Язык: Английский

Процитировано

8

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

и другие.

ACS Applied Materials & Interfaces, Год журнала: 2025, Номер unknown

Опубликована: Март 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

Язык: Английский

Процитировано

0

Development of a biphasic catalytic system for Ullmann coupling hydroxylation of 2,6-dichlorotoluene DOI
Long Zhang,

Yuran Cheng,

G XU

и другие.

Surfaces and Interfaces, Год журнала: 2025, Номер unknown, С. 106382 - 106382

Опубликована: Апрель 1, 2025

Язык: Английский

Процитировано

0

Manifestation of Size Heterogeneity of Molecular Aggregates in the Distribution of Their Fluorescence Lifetimes and Diffusion Coefficients DOI
A. Kasem Chowdhury, Anindya Datta

The Journal of Physical Chemistry C, Год журнала: 2025, Номер 129(18), С. 8708 - 8716

Опубликована: Март 5, 2025

Microscopic insights into molecular aggregation have been obtained using R1, a model solvatochromic fluorophore in DMF–water mixtures. Fluorescence quantum yield (ϕf) and lifetime (τf) of R1 decrease monotonically up to rather high molar ratio water (χH2O). Near invariance the hydrodynamic radius, estimated fluorescence correlation spectroscopy, assigns this progressive increase polarity medium not aggregation. An abrupt ϕf beyond critical χH2O marks onset R1. Concomitantly, decays become bimodal, with emergence longer component associated aggregates. Significant heterogeneity is observed distribution lifetimes, indicating existence aggregates different kinds. quenching, upon further χH2O, assigned breakdown smaller ones. A qualitative between size τf by imaging microscopy.

Язык: Английский

Процитировано

0

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

Pritesh Keshari,

Rajan Yadav,

Priya Mata

и другие.

ACS Sustainable Chemistry & Engineering, Год журнала: 2024, Номер 12(31), С. 11473 - 11479

Опубликована: Июль 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.

Язык: Английский

Процитировано

3

Core-Labeled Reverse Micelle-Based Supramolecular Solvents for Assisted Quick and Sensitive Determination of Amitriptyline in Wastewater DOI
Arun Sharma, Gagandeep Singh, Navneet Kaur

и другие.

Langmuir, Год журнала: 2024, Номер unknown

Опубликована: Фев. 6, 2024

In recent years, the issue of pharmaceutical contaminants in water bodies has emerged as a significant environmental concern owing to potential negative impacts on both aquatic ecosystems and human health. Consequently, development efficient eco-friendly methods for their determination removal is paramount importance. this context, surfactant ensemble sensor been explored hard-to-sense amphiphilic drug, i.e., amitriptyline. Herein, pyrene-based amphiphile chemoreceptor was synthesized characterized through various spectroscopic techniques such 1H, 13C NMR, single-crystal XRD, FTIR, ES-mass spectrometry. Then, dodecanoic acid (DA) receptor THF/water solvent system were used generate reverse micelle-based self-aggregates SUPRAS (SUPRAmolecular Solvent). The structural aspects, morphology size, along with stability aggregates unfolded microscopic insights. present investigation describes synergistic approach that combines unique properties premicellar concentration supramolecular promising enhanced amitriptyline extraction simultaneous from (LOD = 12 nM). To evaluate effectiveness developed real-world scenarios, experiments conducted determine sensing efficiency among pollutants commonly found sources. results reveal nanoensemble exhibits remarkable ability, toward (AMT) drug outperforming conventional methods.

Язык: Английский

Процитировано

2

Refolding SDS-mediated partially-unfolded proteins: A distinguishing role of tetraalkylammonium ionic liquids via mixed micellar aggregation DOI
Rajkumar Sahoo,

Prabal Pramanik,

Mintu Halder

и другие.

Journal of Photochemistry and Photobiology A Chemistry, Год журнала: 2024, Номер 454, С. 115661 - 115661

Опубликована: Апрель 13, 2024

Язык: Английский

Процитировано

2