Surfactant Assemblies as Nanoreactors for Organic Transformations DOI
Margery Cortes‐Clerget, Joseph R. A. Kincaid, Nnamdi Akporji

et al.

Supramolecular Catalysis, Journal Year: 2021, Volume and Issue: unknown, P. 467 - 487

Published: Dec. 31, 2021

This chapter discusses how micellar catalysis based on "designer" surfactants in water provides an attractive alternative to the use of organic solvents. The unique properties aqueous nanomicelles enable transformations under mild and sustainable conditions also provide opportunities for multistep processes a one-pot sequence. Numerous transformations, including cross-couplings, amide bond formation, biocatalysis, are presented, as selected industrial applications which economic environmental benefits readily apparent.

Language: Английский

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

Jagdeep K. Virdi,

Ashish Dusunge,

Sachin Handa

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(2), P. 301 - 317

Published: Jan. 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.

Language: Английский

Citations

29
Palladium-catalyzed micellar cross-couplings: An outlook DOI Creative Commons
Tharique N. Ansari, Fabrice Gallou, Sachin Handa

et al.

Coordination Chemistry Reviews, Journal Year: 2023, Volume and Issue: 488, P. 215158 - 215158

Published: May 2, 2023

Language: Английский

Citations

30
Recent Advances in Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions: Exploration of Catalytic Systems, Reaction Parameters, and Ligand Influences: A Review DOI
Dana A. Kader,

Mohammed Koksh Sidiq,

Salam Ghafour Taher

et al.

Journal of Organometallic Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 123569 - 123569

Published: Feb. 1, 2025

Language: Английский

Citations

1
A General Kilogram Scale Protocol for Suzuki–Miyaura Cross-Coupling in Water with TPGS-750-M Surfactant DOI
Michaël Parmentier,

Mona Wagner,

Regina Wickendick

et al.

Organic Process Research & Development, Journal Year: 2020, Volume and Issue: 24(8), P. 1536 - 1542

Published: July 15, 2020

The development of a kilogram scale protocol for Suzuki–Miyaura cross-coupling step toward the synthesis drug candidate LSZ102 is described. Particularly, use surfactant TPGS-750-M in water as medium transformation and its impact on selectivity quality are reported. Minimization typical impurities generated during (e.g., dehalogenation) has been focus our study. environmental cost impacts using such process also discussed.

Language: Английский

Citations

55
Surfactant Micellar and Vesicle Microenvironments and Structures under Synthetic Organic Conditions DOI
Hannah Peacock, Suzanne A. Blum

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(13), P. 7648 - 7658

Published: March 23, 2023

Fluorescence lifetime imaging microscopy (FLIM) reveals vesicle sizes, structures, microenvironments, reagent partitioning, and system evolution with two chemical reactions for widely used surfactant-water systems under conditions relevant to organic synthesis, including during steps of Negishi cross-coupling reactions. In contrast previous investigations, the present experiments characterize surfactant representative organohalide substrates at high concentrations (0.5 M) that are reflective preparative-scale performed reported in water. presence substrates, 2-iodoethylbenzene 2-bromo-6-methoxypyridine, micelles swell into emulsion droplets up 20 μm diameter, which is 3-4 orders magnitude larger than previously measured absence an substrate (5-200 nm). The partitioning reagents these imaged through FLIM─demonstrated here nonpolar, amphiphilic, organic, basic, oxidative-addition reactive compounds, a zinc metal powder, palladium catalyst. FLIM characterizes species and/or provides microenvironment information inside vesicles. These data show surfactants cause surfactant-dictated microenvironments smaller (<200 nm) but addition produces internal dictated primarily by rather surfactant, concurrent swelling. Addition catalyst causes environments differ between vesicles─information not available nor predicted from prior analytical techniques. Together, provide immediately actionable revising reaction models underpin development sustainable chemistry

Language: Английский

Citations

22
Selectivity in micellar catalysed reactions: The role of interfacial dipole, compartmentalisation, and specific interactions with the surfactants DOI Creative Commons
Sara Mattiello, Erika Ghiglietti, Anita Zucchi

et al.

Current Opinion in Colloid & Interface Science, Journal Year: 2023, Volume and Issue: 64, P. 101681 - 101681

Published: Feb. 13, 2023

Micellar catalysis is playing a major role in green chemistry with ever increasing applications the efficient and sustainable preparation of natural compounds, drugs, more recently organic semiconductors for printed electronics.Most contributions field focus on developments surfactants suitable formulative conditions capable reproducingand often improvingthe yield reactions commonly performed solvents.The real ambition micellar approach goes beyond improvement sustainability existing methods aims at mimicking not only efficiency but also selectivity enzymatic catalysis.This review summarizes relevant examples enabled, efficient, selective transformations, discusses different kind processes impacting product distribution depending details state achieved.

Language: Английский

Citations

19
Chemoselective Reductive Aminations in Aqueous Nanoreactors Using Parts per Million Level Pd/C Catalysis DOI

Ruchita R. Thakore,

Balaram S. Takale, Gianluca Casotti

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(16), P. 6324 - 6329

Published: Aug. 3, 2020

Condensation in recyclable water between aldehydes or ketones and amines occurs smoothly within the hydrophobic cores of nanomicelles, resulting imine formation that is subject to subsequent reduction leading, overall, reductive amination. This micellar technology enables synthesis several types pharmaceuticals, a new procedure relies on only 2000 ppm (0.20 mol %) palladium from commercially available Pd/C. A broad range substrates can be used under mild conditions, leading high chemical yields desired secondary tertiary amines.

Language: Английский

Citations

43
Environmentally responsible, safe, and chemoselective catalytic hydrogenation of olefins: ppm level Pd catalysis in recyclable water at room temperature DOI
Balaram S. Takale,

Ruchita R. Thakore,

Eugene S. Gao

et al.

Green Chemistry, Journal Year: 2020, Volume and Issue: 22(18), P. 6055 - 6061

Published: Jan. 1, 2020

Textbook catalytic hydrogenations are typically presented as reactions done in organic solvents and oftentimes under varying pressures of hydrogen using specialized equipment.

Language: Английский

Citations

40
Mild and Robust Stille Reactions in Water using Parts Per Million Levels of a Triphenylphosphine‐Based Palladacycle DOI
Balaram S. Takale,

Ruchita R. Thakore,

Gianluca Casotti

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 60(8), P. 4158 - 4163

Published: Nov. 12, 2020

Abstract An inexpensive and new triphenylphosphine‐based palladacycle has been developed as a pre‐catalyst, leading to highly effective Stille cross‐coupling reactions in water under mild reaction conditions. Only 500–1000 ppm of Pd suffices for couplings involving variety aryl/heteroaryl halides with aryl/hetaryl stannanes. Several drug intermediates can be prepared using this catalyst aqueous nanoreactors formed by 2 wt % Brij‐30 water.

Language: Английский

Citations

39
Shielding Effect of Nanomicelles: Stable and Catalytically Active Oxidizable Pd(0) Nanoparticle Catalyst Compatible for Cross-Couplings of Water-Sensitive Acid Chlorides in Water DOI Creative Commons
Tharique N. Ansari, Sudripet Sharma, Susanta Hazra

et al.

JACS Au, Journal Year: 2021, Volume and Issue: 1(9), P. 1506 - 1513

Published: July 20, 2021

Under the shielding effect of nanomicelles, a sustainable micellar technology for design and convenient synthesis ligand-free oxidizable ultrasmall Pd(0) nanoparticles (NPs) their subsequent catalytic exploration couplings water-sensitive acid chlorides in water is reported. A proline-derived amphiphile, PS-750-M, plays crucial role stabilizing these NPs, preventing aggregation oxidation state changes. These NPs were characterized using 13C nuclear magnetic resonance (NMR), infrared (IR), surface-enhanced Raman scattering (SERS) spectroscopy to evaluate carbonyl interactions PS-750-M with Pd. High-resolution transmission electron microscopy (HRTEM) energy-dispersive X-ray (EDX) studies performed reveal morphology, particle size distribution, chemical composition, whereas photoelectron (XPS) measurements unveiled metal. In cross-couplings boronic acids, micelle's acids vital unwanted side reactions, including hydrolysis under basic pH. This approach scalable applications are showcased multigram scale reactions.

Language: Английский

Citations

32