Reactivity of Styrenes in Micelles: Safe, Selective, and Sustainable Functionalization with Azides and Carboxylic Acids

Hazra, Susanta; Kaur, Gaganpreet; Handa, Sachin

doi:10.1021/acssuschemeng.1c01577

Cited by 12 publications

(4 citation statements)

References 58 publications

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“…Harmful dipolar-aprotic solvents such as DMF, DMAc, NMP, or 1,4-dioxane are quite often used in organic synthesis. Hazra et al studied the oxyfunctionalization of styrene in micellar solutions of the designer surfactant PS-750-M [ 69 ]. The surfactant was designed to structurally mimic the named solvents and, depending on the applied nucleophile (Nu), azidoketones (Nu = N 3 ) or acyloxyketones (Nu = PhCO 2 ) were obtained on a gram scale with yields in the range of 60 to 80%.…”

Section: Discussionmentioning

confidence: 99%

Is Micellar Catalysis Green Chemistry?

et al. 2023

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Many years ago, twelve principles were defined for carrying out chemical reactions and processes from a green chemistry perspective. It is everyone’s endeavor to take these points into account as far as possible when developing new processes or improving existing ones. Especially in the field of organic synthesis, a new area of research has thus been established: micellar catalysis. This review article addresses the question of whether micellar catalysis is green chemistry by applying the twelve principles to micellar reaction media. The review shows that many reactions can be transferred from an organic solvent to a micellar medium, but that the surfactant also has a crucial role as a solubilizer. Thus, the reactions can be carried out in a much more environmentally friendly manner and with less risk. Moreover, surfactants are being reformulated in their design, synthesis, and degradation to add extra advantages to micellar catalysis to match all the twelve principles of green chemistry.

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Section: Discussionmentioning

confidence: 99%

Is Micellar Catalysis Green Chemistry?

et al. 2023

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“…In this way, compatibility between micellar media and visible light heterogeneous photocatalysis was established to oxidize benzylic alcohols into aldehydes (Scheme 7). 33 The creation of a heterogeneous polymeric Cu( i ) based on a perylene diimide (PDI) unit allows the oxidation of alcohol through the Cu( i )–Cu( ii ) cycle in the presence of co-catalytic TEMPO under air and visible light. As this polymer was insoluble in organic solvents, recyclability was demonstrated for this transformation, delivering aldehydes in mostly good-to-excellent yields.…”

Section: Design Applications and Insights Into Micellar Technologymentioning

confidence: 99%

Aqueous micellar technology: an alternative beyond organic solvents

et al. 2023

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“…The product was isolated by extraction with ethyl acetate. Notably, the tandem reactions could be performed on a gram scale [ 136 ].…”

Section: Multistep One-pot Reactionsmentioning

confidence: 99%

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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Reactivity of Styrenes in Micelles: Safe, Selective, and Sustainable Functionalization with Azides and Carboxylic Acids

Cited by 12 publications

References 58 publications

Is Micellar Catalysis Green Chemistry?

Is Micellar Catalysis Green Chemistry?

Aqueous micellar technology: an alternative beyond organic solvents

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

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