Organic synthesis in Aqueous Multiphase Systems — Challenges and opportunities ahead of us

Hauk, Pascal; Wencel‐Delord, Joanna; Ackermann, Lutz; Walde, Peter; Gallou, Fabrice

doi:10.1016/j.cocis.2021.101506

Cited by 38 publications

(33 citation statements)

References 54 publications

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“…15 In this direction, new surfactants are incessantly being engineered to compete with traditional nickel catalysis in organic solvents as a safer approach. 16…”

Section: Resultsmentioning

confidence: 99%

‘In-water’, nickel-catalyzed mild preparation of allylic amines employing alcohols: application to ‘all-water’ synthesis of pharmaceuticals

et al. 2022

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“…15 In this direction, new surfactants are incessantly being engineered to compete with traditional nickel catalysis in organic solvents as a safer approach. 16…”

Section: Resultsmentioning

confidence: 99%

‘In-water’, nickel-catalyzed mild preparation of allylic amines employing alcohols: application to ‘all-water’ synthesis of pharmaceuticals

et al. 2022

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“…To date, this understanding for each system has been empirical. Increased use of computational tools to understand how the surfactant affects the performance of a given system (surfactant, catalyst, and reaction) could considerably accelerate this technology [ 62 ].…”

Section: Discussionmentioning

confidence: 99%

“…Such nonionic surfactants include PEGylated amphiphiles, such as TPGS-750-M and PTS, which yield spherical micelles, as well as Nok, which yields rod-like micelles ( Figure 1 ). Micelles with dimensions on the order of 50–60 nm are considered ideal for accommodating exchange of reactants, products, etc., with a sufficient hydrophobic microenvironment to facilitate the reaction [ 62 ].…”

Section: Designer Surfactantsmentioning

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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“… 236 For further details, an excellent review discussing the challenges and opportunities faced by aqueous-micellar organic synthesis was published in 2021 in collaboration with Novartis (Gallou et al). 237 …”

Section: Selection Of Alternative Solventsmentioning

confidence: 99%

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

et al. 2022

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Dipolar aprotic and ethereal solvents comprise just over 40% of all organic solvents utilized in synthetic organic, medicinal, and process chemistry. Unfortunately, many of the common “go-to” solvents are considered to be “less-preferable” for a number of environmental, health, and safety (EHS) reasons such as toxicity, mutagenicity, carcinogenicity, or for practical handling reasons such as flammability and volatility. Recent legislative changes have initiated the implementation of restrictions on the use of many of the commonly employed dipolar aprotic solvents such as dimethylformamide (DMF) and N -methyl-2-pyrrolidinone (NMP), and for ethers such as 1,4-dioxane. Thus, with growing legislative, EHS, and societal pressures, the need to identify and implement the use of alternative solvents that are greener, safer, and more sustainable has never been greater. Within this review, the ubiquitous nature of dipolar aprotic and ethereal solvents is discussed with respect to the physicochemical properties that have made them so appealing to synthetic chemists. An overview of the current legislative restrictions being imposed on the use of dipolar aprotic and ethereal solvents is discussed. A variety of alternative, safer, and more sustainable solvents that have garnered attention over the past decade are then examined, and case studies and examples where less-preferable solvents have been successfully replaced with a safer and more sustainable alternative are highlighted. Finally, a general overview and guidance for solvent selection and replacement are included in the Supporting Information of this review.

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Organic synthesis in Aqueous Multiphase Systems — Challenges and opportunities ahead of us

Cited by 38 publications

References 54 publications

‘In-water’, nickel-catalyzed mild preparation of allylic amines employing alcohols: application to ‘all-water’ synthesis of pharmaceuticals

‘In-water’, nickel-catalyzed mild preparation of allylic amines employing alcohols: application to ‘all-water’ synthesis of pharmaceuticals

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

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

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