Introducing Savie: A Biodegradable Surfactant Enabling Chemo- and Biocatalysis and Related Reactions in Recyclable Water

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(7), P. 4266 - 4278

Published: Feb. 8, 2023

Savie is a biodegradable surfactant derived from vitamin E and polysarcosine (PSar) developed for use in organic synthesis recyclable water. This includes homogeneous catalysis (including examples employing only ppm levels of catalyst), heterogeneous catalysis, biocatalytic transformations, including multistep chemoenzymatic sequence. Use frequently leads to significantly higher yields than do conventional surfactants, while obviating the need waste-generating solvents.

Language: Английский

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Aqueous Micelles as Solvent, Ligand, and Reaction Promoter in Catalysis

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

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Towards a sustainable tomorrow: advancing green practices in organic chemistry

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(11), P. 6289 - 6317

Published: Jan. 1, 2024

Chemistry in water, leveraging its solvent properties, provides a safer and more sustainable alternative to traditional organic methods.

Language: Английский

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Aqueous micellar technology: an alternative beyond organic solvents

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(20), P. 2842 - 2853

Published: Jan. 1, 2023

Solvents are the major source of chemical waste from synthetic chemistry labs.

Language: Английский

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Gold and palladium supported on an ionic liquid modified Fe-based metal–organic framework (MOF) as highly efficient catalysts for the reduction of nitrophenols, dyes and Sonogashira–Hagihara reactions

RSC Advances, Journal Year: 2023, Volume and Issue: 13(12), P. 8101 - 8113

Published: Jan. 1, 2023

Novel supported noble metals, on an ionic liquid modified Fe-based metal–organic framework (MOF), are considered as efficient catalyst.

Language: Английский

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Surfactant Micellar and Vesicle Microenvironments and Structures under Synthetic Organic Conditions

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

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Recent Highlights in Micellar Catalysis: An Industrial Outlook

Organic Process Research & Development, Journal Year: 2024, Volume and Issue: 28(4), P. 816 - 830

Published: March 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.

Language: Английский

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On the role of surfactants: rethinking “aqueous” chemistry

Green Chemistry, Journal Year: 2023, Volume and Issue: 26(2), P. 739 - 752

Published: Dec. 11, 2023

Some of the latest technological developments involving chemistry in water are discussed.

Language: Английский

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Nanoparticles as Heterogeneous Catalysts for ppm Pd-Catalyzed Aminations in Water

ACS Sustainable Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 12(5), P. 1997 - 2008

Published: Jan. 22, 2024

A general protocol employing heterogeneous catalysis has been developed that enables ppm of Pd-catalyzed C-N cross-coupling reactions under aqueous micellar catalysis. new nanoparticle catalyst containing specifically ligated Pd, in combination with nanoreactors composed the designer surfactant Savie, a biodegradable amphiphile, catalyzes bond formations recyclable water. variety coupling partners, ranging from highly functionalized pharmaceutically relevant APIs to educts Merck Informer Library, readily participate these environmentally responsible, sustainable reaction conditions. Other key features associated this report include low levels residual Pd found products, recyclability medium, use ocean water as an alternative source options for pseudohalides and

Language: Английский

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Simplified Preparation of ppm Pd-Containing Nanoparticles as Catalysts for Chemistry in Water

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(5), P. 3179 - 3186

Published: Feb. 17, 2023

A protocol has been developed that not only simplifies the preparation of nanoparticles (NPs) containing ppm levels ligated palladium affect heterogeneous catalysis but also ensures they afford products cross-couplings reproducibly due to freshly prepared nature each reagent. Four different types couplings are studied: Suzuki-Miyaura, Sonogashira, Mizoroki-Heck, and Negishi reactions, all performed under mild aqueous micellar conditions. The simplified process relies on initial formation stable, storable Pd- ligand-free NPs, which is then added appropriate amount Pd(OAc)2 ligand-matched desired type coupling, in water.

Language: Английский

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