Micellar nanoreactors for organic transformations with a focus on “dehydration” reactions in water: A decade update

Banerjee, Mainak; Panjikar, Padmini C.; Bhutia, Zigmee T.; Bhosle, Akhil A.; Chatterjee, Amrita

doi:10.1016/j.tet.2021.132142

Cited by 24 publications

(23 citation statements)

References 347 publications

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“…However, recycling and recovery of materials with maintained catalytic performance remain a key challenge [ 13 ]. Whereas reuse of micellar systems for multiple cycles is commonly reported [ 162 ], catalyst deactivation can occur [ 103 , 108 ]. Additional catalyst may be needed for subsequent cycles [ 41 , 64 ].…”

Section: Discussionmentioning

confidence: 99%

“…Practically, in addition to reaction scale, the separation and isolation of the product as well, as reuse of the catalyst, are important considerations. The use of water as a solvent can enable catalyst recycling using biphasic extraction [ 162 ]. However, product extraction can be challenging due to the volume of the organic solvent used.…”

Section: Process Innovationsmentioning

confidence: 99%

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Cascade Processes with Micellar Reaction Media: Recent Advances and Future Directions

Tang

McInnes

2022

Molecules

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

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Section: Discussionmentioning

confidence: 99%

Section: Process Innovationsmentioning

confidence: 99%

Cascade Processes with Micellar Reaction Media: Recent Advances and Future Directions

Tang

McInnes

2022

Molecules

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“…It has been demonstrated that micelles have solubilizing effects and can promote catalysis by binding to the substrate through hydrogen bonding, van der Waals forces, or electrostatic gravitational forces. [29][30][31][32] In addition, micelle aggregates of nanometer dimensions behaved as containers in which a variety of reactions occur. Nanometersized micelles increased the local concentration of reactants around their surfaces, which was also one of the reasons for the accelerated transformation.…”

Section: Mechanism Of Two-electron Oxidation Of Tmb To Understand The...mentioning

confidence: 99%

“…[26][27][28] Surfactants can acquire potential enzyme-like active sites through self-assembly and bind to substrates through hydrogen bonding, van der Waals forces, or hydrophobic interactions to form a substrate activation state, ultimately facilitating the reaction of the substrate. [29][30] Moreover, micelles could solubilize many substances in an aqueous solution, thus catalyzing reactions by using the solubilization, stabilization, and sensitization of micelle systems. [31][32] Therefore, we reason that developing a micellar nanozyme would provide a potential benign solution for addressing the instability of TMB oxidation in bioassay by HRP.…”

Section: Introductionmentioning

confidence: 99%

Enhancing Reliability of Chromogenic Bioassay with Two-Electron TMB Oxidation Enabled by Self-assembled Surfactants Nanozyme

Zhu¹,

Xu²,

Hong³

et al. 2022

Preprint

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In a standard colorimetric sensing assay based on HRP-H2O2-TMB (3,3’,5,5’-tetramethylbenzidine), the stability of the signal of the chromogenic probe (TMBox) is essential for the accuracy of measurements. Terminators, typically of strong acids, are often added to maintain signal stability. However, additional manipulations may compromise sensing accuracy and the use of strong acids cause safety hazards. Here, a self-assembled sodium dodecyl sulfate (SDS) micellar nanozymes sensing strategy was proposed, which can catalyze the two-electron oxidization of TMB directly to the final state. Unlike the free and bound oxygen intermediates pathways, the micellar nanozymes enabled a microenvironment conducive to two-electron oxidization of TMB, in which the electrostatic attraction between the micellar nanozymes and TMB played crucial roles in substrate activation and intermediates stabilization. It allows micellar nanozyme to remain active even at very high H2O2 concentrations, thus enabling a broader detection range. GOD and the micellar nanozymes were cascaded for glucose detection as an application. As a result, the disadvantage of signal instability in conventional glucose biosensors from natural enzyme systems (HRP and GOD) was avoided.

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“…Micelle‐aided organic transformations has become widely used both in academical research and industrial applications in the last few years, [4] as the use of surfactants allows the implementation of several organic synthetic methods in aqueous media under mild conditions. Not surprisingly, micellar conditions have found application in DEL chemistry as well.…”

Section: Introductionmentioning

confidence: 99%

The Potential of Micellar Media in the Synthesis of DNA‐Encoded Libraries

Novàk

Adamik

Buchholcz

et al. 2022

Chemistry A European J

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DNA-encoded library (DEL) technology has become widely used in drug discovery research. The construction of DELs requires robust organic transformations that proceed in aqueous media under mild conditions. Unfortunately, the application of water as reaction medium for organic synthesis is not evident due to the generally limited solubility of organic reagents. However, the use of surfactants can offer a solution to this issue. Oil-in-water microemulsions formed by surfactant micelles are able to localize hydrophobic reagents inside them, resulting in high local concentrations of the organic substances in an otherwise poorly solvated environment. This review provides a conceptual and critical summary of micellar synthesis possibilities that are well suited to DEL synthesis. Existing examples of micellar DEL approaches, together with a selection of micellar organic transformations fundamentally suitable for DEL are discussed.

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Micellar nanoreactors for organic transformations with a focus on “dehydration” reactions in water: A decade update

Cited by 24 publications

References 347 publications

Cascade Processes with Micellar Reaction Media: Recent Advances and Future Directions

Cascade Processes with Micellar Reaction Media: Recent Advances and Future Directions

Enhancing Reliability of Chromogenic Bioassay with Two-Electron TMB Oxidation Enabled by Self-assembled Surfactants Nanozyme

The Potential of Micellar Media in the Synthesis of DNA‐Encoded Libraries

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